Monticello Wine Week 2025
Celebrate the vibrant flavors and rich heritage of Virginia wine at Monticello Wine Week 2025, the region’s premier wine festival showcasing the best of the Monticello AVA - recently named Wine Region of the Year by Wine Enthusiast. Over four unforgettable days, immerse yourself in exclusive tastings, elegant winemaker dinners, lively picnics, and sparkling brunches hosted across some of Virginia’s most stunning vineyards and venues.
Meet passionate winemakers dedicated to crafting award-winning wines, savor thoughtfully paired gourmet cuisine, and enjoy live music and breathtaking views of the Blue Ridge Mountains. Whether you’re a seasoned oenophile or new to Virginia’s wine country, Monticello Wine Week offers a perfect blend of education, celebration, and community in an inspiring setting. Don’t miss this chance to experience the heart and soul of Virginia’s wine country like never before!
If you want, I can also help craft descriptions for specific events within the week!
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Entertainment. Couples. Contact: Monticello Wine Trail. Contact Phone: (434) 566-6117.
Thursday, June 5, 2025 – Sunday, June 8, 2025.
For more info visit monticellowinetrail.com. Fridays After Five
Fridays After Five is Charlottesville’s signature free summer concert series, bringing the community together every Friday evening at Ting Pavilion on the Downtown Mall. Enjoy live performances from a diverse lineup of local and regional bands, spanning genres from rock and pop to soul, bluegrass, and more. Bring your friends and family, grab food and drinks from local vendors, and start your weekend with great music in a lively, family-friendly atmosphere. Rain or shine, it’s the place to be for music lovers and anyone looking for a fun, social Friday night out in the heart of Charlottesville.
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Art & Culture. Entertainment. Contact: Ting Pavilion. Contact Phone: (434) 245-4910.
Friday, June 6, 2025, 5:30 PM – 8:30 PM.
For more info visit www.tingpavilion.com. Chris Stapleton’s All-American Road Show
Experience Grammy-winning country artist Chris Stapleton live as he brings his acclaimed All-American Road Show to Charlottesville for two nights at John Paul Jones Arena. Known for his powerful vocals, soulful songwriting, and electrifying stage presence, Stapleton’s concerts are celebrated for their authenticity and emotional depth. Special guest Nikki Lane will open the show. Expect a setlist packed with hits like “Tennessee Whiskey,” “Broken Halos,” and “Starting Over,” all delivered with Stapleton’s signature blend of country, rock, and blues.
The show features mobile entry tickets only, a clear bag policy, and a list of prohibited items (see venue website for full details).
Event Type: Local Event. Event Category: Art & Culture. Entertainment. Contact: John Paul Jones Arena. Contact Phone: (434) 243-4960.
Friday, June 6, 2025, 7:30 PM – 10:30 PM.
295 Massie Rd, Charlottesville, VA 22903.
For more info visit www.johnpauljonesarena.com. Virginia Renaissance Faire
Step back in time at the Virginia Renaissance Faire, celebrating its 23rd season in 2025! Held over five weekends at Lake Anna Winery, this lively festival brings the magic and adventure of the Renaissance to life with jousting, live combat, archery demonstrations, artisan markets, blacksmithing, costumed performers, and themed entertainment. Enjoy Celtic music and dance, pirate invasions, romance, and family-friendly activities like puppet shows and butterfly dancing. Savor delicious festival fare-from turkey legs to funnel cakes-and shop for unique handmade goods, jewelry, costumes, and more. The faire is a beloved tradition for all ages, offering a full day of revelry, history, and fun.
10:00 AM – 5:00 PM each day.
Property: Omni Charlottesville Hotel. Event Type: Local Event. Contact: Lake Anna Winery. Contact Phone: (703) 508-5036.
Saturday, June 7, 2025 – Sunday, June 8, 2025.
For more info visit varf.org. Charlottesville City Market
Charlottesville’s oldest open-air market is back! We offer a little bit of everything. Fresh fruits and veggies, handmade crafts, homemade baked goods, fresh roasted coffee, doughnuts, organic bagels, authentic cultural foods made on location, fresh artisan breads, and much more. You must visit the market; it is truly a taste of Charlottesville.
Event Type: Local Event. Event Category: Entertainment. Family. Holiday. Wellness & Fitness. Couples. Contact: Charlottesville Parks & Recreation. Contact Phone: 434-970-3260.
Saturday, June 7, 2025, 8:00 AM – 1:00 PM.
100 Water Street
Charlottesville, VA 22902.
For more info visit www.charlottesville.gov. Chris Stapleton’s All-American Road Show
Experience Grammy-winning country artist Chris Stapleton live as he brings his acclaimed All-American Road Show to Charlottesville for two nights at John Paul Jones Arena. Known for his powerful vocals, soulful songwriting, and electrifying stage presence, Stapleton’s concerts are celebrated for their authenticity and emotional depth. Special guest Nikki Lane will open the show. Expect a setlist packed with hits like “Tennessee Whiskey,” “Broken Halos,” and “Starting Over,” all delivered with Stapleton’s signature blend of country, rock, and blues.
The show features mobile entry tickets only, a clear bag policy, and a list of prohibited items (see venue website for full details).
Event Type: Local Event. Event Category: Art & Culture. Entertainment. Contact: John Paul Jones Arena. Contact Phone: (434) 243-4960.
Saturday, June 7, 2025, 7:30 PM – 10:30 PM.
295 Massie Rd, Charlottesville, VA 22903.
For more info visit www.johnpauljonesarena.com. King Family Vineyards (Roseland Polo Club)
Every Sunday from Memorial Day weekend (May 25, 2025) through mid-October (October 12, 2025), weather permitting
Regular match time: 12:00 PM (noon)
Gates open: 10:00 AM
Special summer schedule (July 6 – August 3, 2025): Matches at 5:00 PM and 6:30 PM; gates open at 4:00 PM
Experience the elegance and excitement of polo every Sunday at King Family Vineyards, set against the stunning backdrop of the Blue Ridge Mountains. Watch thrilling polo matches featuring skilled players and their magnificent ponies on the vineyard’s lush fields. Arrive early to enjoy tailgating with family and friends-set up your own space or reserve a spot with or without a tent for shade. Sip award-winning King Family wines, savor food from local vendors, and soak in the festive, welcoming atmosphere. The matches are perfect for all ages, whether you’re a polo enthusiast or new to the sport. During the hottest weeks in July, matches shift to cooler evening times to enhance your comfort. Reservations are recommended for tailgating spaces…
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Wellness & Fitness. Contact: King Family Vineyards. Contact Phone: (434) 823-7800.
Sunday, June 8, 2025, 10:00 AM – 2:00 PM.
For more info visit kingfamilyvineyards.com. Farmers in the Park
Charlottesville’s oldest open-air market is back! We offer a little bit of everything. Fresh fruits and veggies, handmade crafts, homemade baked goods, fresh roasted coffee, doughnuts, organic bagels, authentic cultural foods made on location, fresh artisan breads, and much more. You must visit the market; it is truly a taste of Charlottesville.
Event Type: Local Event. Contact: Charlottesville Parks & Recreation. Contact Phone: 434-970-3260.
Wednesday, June 11, 2025, 3:00 PM – 7:00 PM.
Pen Park
1300 Pen Park Road
Charlottesville, VA 22901.
For more info visit www.charlottesville.gov. Fridays After Five
Fridays After Five is Charlottesville’s signature free summer concert series, bringing the community together every Friday evening at Ting Pavilion on the Downtown Mall. Enjoy live performances from a diverse lineup of local and regional bands, spanning genres from rock and pop to soul, bluegrass, and more. Bring your friends and family, grab food and drinks from local vendors, and start your weekend with great music in a lively, family-friendly atmosphere. Rain or shine, it’s the place to be for music lovers and anyone looking for a fun, social Friday night out in the heart of Charlottesville.
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Art & Culture. Entertainment. Contact: Ting Pavilion. Contact Phone: (434) 245-4910.
Friday, June 13, 2025, 5:30 PM – 8:30 PM.
For more info visit www.tingpavilion.com. James River Batteau Festival (40th Annual)
The James River Batteau Festival is a unique eight-day paddling event and heritage celebration tracing the historic route of batteaux boats on the James River. Each day, participants launch in the morning (around 8–10 AM) and paddle scenic stretches of the river, arriving at riverside camps by late afternoon. Evening festivities start around 5:00 PM and include live music, storytelling, communal dinners, and socializing in a family-friendly atmosphere.
Dates and Time:
Saturday, June 14 – Saturday, June 21, 2025
Daily river paddling segments start in the morning (typically 8:00 AM – 10:00 AM) and continue through the afternoon. Evening festivities begin around 5:00 PM at each riverside camp.
Tickets and Fees:
Paddler Registration: $150 for the full week (includes camping, dinners, and festival participation)
Daily Paddler Pass: $30 per day (includes camping and dinner for that day)
Dinner Only: $15 per person (available to non-paddlers joining evening festivities)
Camping: Included with paddler registration…
Property: Omni Charlottesville Hotel. Event Type: Local Event. Contact: Multi-day, multi-location event along the James River. Contact Phone: (804) 397-5357.
Saturday, June 14, 2025 – Saturday, June 21, 2025.
For more info visit www.vacanals.org. Charlottesville City Market
Charlottesville’s oldest open-air market is back! We offer a little bit of everything. Fresh fruits and veggies, handmade crafts, homemade baked goods, fresh roasted coffee, doughnuts, organic bagels, authentic cultural foods made on location, fresh artisan breads, and much more. You must visit the market; it is truly a taste of Charlottesville.
Event Type: Local Event. Event Category: Entertainment. Family. Holiday. Wellness & Fitness. Couples. Contact: Charlottesville Parks & Recreation. Contact Phone: 434-970-3260.
Saturday, June 14, 2025, 8:00 AM – 1:00 PM.
100 Water Street
Charlottesville, VA 22902.
For more info visit www.charlottesville.gov. Know Good Beer & Bourbon Festival
The Know Good Beer & Bourbon Festival is Charlottesville’s premier tasting event for craft beer and bourbon enthusiasts. Sample an extensive selection of local, regional, and national craft beers alongside a curated lineup of bourbons and whiskeys. Enjoy live music, food trucks, and a lively festival atmosphere in the creative hub of IX Art Park. The event is 21+ and offers the perfect blend of discovery, fun, and flavor for anyone passionate about craft beverages.
Property: Omni Charlottesville Hotel. Event Type: Local Event. Contact: IX Art Park. Contact Phone: (434) 207-2355.
Saturday, June 14, 2025, 4:00 PM – 8:00 PM.
For more info visit www.eventbrite.com. Rivanna Roots Concert Series
Rivanna Roots is a beloved family-friendly outdoor concert series held on the scenic banks of the Rivanna River. Enjoy an evening of outstanding local and regional music in a relaxed riverside setting. Bring your blanket or chair, savor local craft beer, cider, and wine from exclusive beverage partners, and enjoy delicious offerings from rotating food trucks. Kids 12 and under attend free (please add a free children’s ticket for attendance tracking).
Ticket Prices:
$15 in advance
$18 after 5:00 PM the day before the show and at the door
Kids 12 and under: Free (add free children’s ticket for tracking)
Season Pass: $195 full price (early bird $175 sold out) for all 13 concerts
Tickets support the performing artists and music education programs through The Front Porch Music School. Parking on-site is $5 cash per car; free parking options are available nearby. Dogs on leashes are welcome, and outside food is permitted (no outside alcohol). The event is rain or shine.
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Entertainment. Art & Culture. Couples. Contact: Rivanna River Company. Contact Phone: (434) 218-2052.
Saturday, June 14, 2025, 5:00 PM – 9:00 PM.
For more info visit frontporchcville.org. King Family Vineyards (Roseland Polo Club)
Every Sunday from Memorial Day weekend (May 25, 2025) through mid-October (October 12, 2025), weather permitting
Regular match time: 12:00 PM (noon)
Gates open: 10:00 AM
Special summer schedule (July 6 – August 3, 2025): Matches at 5:00 PM and 6:30 PM; gates open at 4:00 PM
Experience the elegance and excitement of polo every Sunday at King Family Vineyards, set against the stunning backdrop of the Blue Ridge Mountains. Watch thrilling polo matches featuring skilled players and their magnificent ponies on the vineyard’s lush fields. Arrive early to enjoy tailgating with family and friends-set up your own space or reserve a spot with or without a tent for shade. Sip award-winning King Family wines, savor food from local vendors, and soak in the festive, welcoming atmosphere. The matches are perfect for all ages, whether you’re a polo enthusiast or new to the sport. During the hottest weeks in July, matches shift to cooler evening times to enhance your comfort. Reservations are recommended for tailgating spaces…
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Wellness & Fitness. Contact: King Family Vineyards. Contact Phone: (434) 823-7800.
Sunday, June 15, 2025, 10:00 AM – 2:00 PM.
For more info visit kingfamilyvineyards.com. Oakencroft Farm Walk
Join Oakencroft Farm Club for a guided walk through their beautiful farm and vineyard. The tour begins in front of the Tasting Room and winds through the vineyard, past the solar array, compost production area, and into the silvopasture. Along the way, you’ll learn about Oakencroft’s commitment to soil health, sustainability, and carbon sequestration in their farming and vineyard management. After the walk, relax in the Tasting Room with a glass of Oakencroft wine or a refreshing summertime spritz. Guests under 21 attend free and can order from the menu as desired. This is a perfect opportunity to experience sustainable agriculture up close and enjoy the scenic beauty of Oakencroft Farm.
Event Type: Local Event. Contact: Oakencroft Farm & Winery. Contact Phone: (434) 234-7066.
Sunday, June 15, 2025, 10:30 AM – 11:30 AM.
915 Oakencroft Farm, Charlottesville, VA 22901.
For more info visit oakencroftfarm.com. Farmers in the Park
Charlottesville’s oldest open-air market is back! We offer a little bit of everything. Fresh fruits and veggies, handmade crafts, homemade baked goods, fresh roasted coffee, doughnuts, organic bagels, authentic cultural foods made on location, fresh artisan breads, and much more. You must visit the market; it is truly a taste of Charlottesville.
Event Type: Local Event. Contact: Charlottesville Parks & Recreation. Contact Phone: 434-970-3260.
Wednesday, June 18, 2025, 3:00 PM – 7:00 PM.
Pen Park
1300 Pen Park Road
Charlottesville, VA 22901.
For more info visit www.charlottesville.gov. Fridays After Five
Fridays After Five is Charlottesville’s signature free summer concert series, bringing the community together every Friday evening at Ting Pavilion on the Downtown Mall. Enjoy live performances from a diverse lineup of local and regional bands, spanning genres from rock and pop to soul, bluegrass, and more. Bring your friends and family, grab food and drinks from local vendors, and start your weekend with great music in a lively, family-friendly atmosphere. Rain or shine, it’s the place to be for music lovers and anyone looking for a fun, social Friday night out in the heart of Charlottesville.
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Art & Culture. Entertainment. Contact: Ting Pavilion. Contact Phone: (434) 245-4910.
Friday, June 20, 2025, 5:30 PM – 8:30 PM.
For more info visit www.tingpavilion.com. Charlottesville Opera Presents: Carmen
Experience the fiery passion and unforgettable melodies of Bizet’s Carmen, one of the world’s most beloved operas. Follow the story of the alluring and free-spirited Carmen as she navigates love, jealousy, and fate in this thrilling production by Charlottesville Opera. With a cast of outstanding vocalists, a full orchestra, and dazzling staging at the historic Paramount Theater, this is a must-see event for opera lovers and newcomers alike. The Saturday matinee features a special cover cast performance, offering a unique interpretation of this timeless classic.
Student/Youth: $15
General Admission: $30, $45, $65, $85 (tiered seating/pricing).
Event Type: Local Event. Event Category: Art & Culture. Couples. Entertainment. Contact: The Paramount Theater. Contact Phone: (434) 979-1333.
Friday, June 20, 2025, 7:30 PM – Saturday, June 21, 2025, 10:30 PM.
215 E Main St, Charlottesville, VA 22902.
For more info visit charlottesville.theparamount.net. Charlottesville City Market
Charlottesville’s oldest open-air market is back! We offer a little bit of everything. Fresh fruits and veggies, handmade crafts, homemade baked goods, fresh roasted coffee, doughnuts, organic bagels, authentic cultural foods made on location, fresh artisan breads, and much more. You must visit the market; it is truly a taste of Charlottesville.
Event Type: Local Event. Event Category: Entertainment. Family. Holiday. Wellness & Fitness. Couples. Contact: Charlottesville Parks & Recreation. Contact Phone: 434-970-3260.
Saturday, June 21, 2025, 8:00 AM – 1:00 PM.
100 Water Street
Charlottesville, VA 22902.
For more info visit www.charlottesville.gov. King Family Vineyards (Roseland Polo Club)
Every Sunday from Memorial Day weekend (May 25, 2025) through mid-October (October 12, 2025), weather permitting
Regular match time: 12:00 PM (noon)
Gates open: 10:00 AM
Special summer schedule (July 6 – August 3, 2025): Matches at 5:00 PM and 6:30 PM; gates open at 4:00 PM
Experience the elegance and excitement of polo every Sunday at King Family Vineyards, set against the stunning backdrop of the Blue Ridge Mountains. Watch thrilling polo matches featuring skilled players and their magnificent ponies on the vineyard’s lush fields. Arrive early to enjoy tailgating with family and friends-set up your own space or reserve a spot with or without a tent for shade. Sip award-winning King Family wines, savor food from local vendors, and soak in the festive, welcoming atmosphere. The matches are perfect for all ages, whether you’re a polo enthusiast or new to the sport. During the hottest weeks in July, matches shift to cooler evening times to enhance your comfort. Reservations are recommended for tailgating spaces…
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Wellness & Fitness. Contact: King Family Vineyards. Contact Phone: (434) 823-7800.
Sunday, June 22, 2025, 10:00 AM – 2:00 PM.
For more info visit kingfamilyvineyards.com. Charlottesville Opera Presents: Carmen
Experience the fiery passion and unforgettable melodies of Bizet’s Carmen, one of the world’s most beloved operas. Follow the story of the alluring and free-spirited Carmen as she navigates love, jealousy, and fate in this thrilling production by Charlottesville Opera. With a cast of outstanding vocalists, a full orchestra, and dazzling staging at the historic Paramount Theater, this is a must-see event for opera lovers and newcomers alike. The Saturday matinee features a special cover cast performance, offering a unique interpretation of this timeless classic.
Student/Youth: $15
General Admission: $30, $45, $65, $85 (tiered seating/pricing).
Event Type: Local Event. Event Category: Art & Culture. Couples. Entertainment. Contact: The Paramount Theater. Contact Phone: (434) 979-1333.
Sunday, June 22, 2025, 2:00 PM – Monday, June 23, 2025, 5:00 PM.
215 E Main St, Charlottesville, VA 22902.
For more info visit charlottesville.theparamount.net. Charlottesville Opera Presents: The Pirates of Penzance
Set sail for laughter and adventure with Gilbert & Sullivan’s comic masterpiece, The Pirates of Penzance! This witty and whimsical operetta tells the tale of Frederic, a young apprentice pirate, who falls in love with the beautiful Mabel and tries to escape the clutches of his bumbling pirate crew. Bursting with clever lyrics, catchy tunes, and hilarious hijinks, this production by Charlottesville Opera promises fun for all ages. Performed with full orchestra and a talented cast, it’s the perfect summer treat for families, opera fans, and anyone looking for a joyous night at the theater.
Student/Youth: $15
General Admission: $30, $45, $65, $85 (tiered seating/pricing).
Event Type: Local Event. Event Category: Art & Culture. Couples. Entertainment. Contact: The Paramount Theater. Contact Phone: (434) 979-1333.
Sunday, June 22, 2025, 7:00 PM – Monday, June 23, 2025, 9:30 PM.
215 E Main St, Charlottesville, VA 22902.
For more info visit charlottesville.theparamount.net. Farmers in the Park
Charlottesville’s oldest open-air market is back! We offer a little bit of everything. Fresh fruits and veggies, handmade crafts, homemade baked goods, fresh roasted coffee, doughnuts, organic bagels, authentic cultural foods made on location, fresh artisan breads, and much more. You must visit the market; it is truly a taste of Charlottesville.
Event Type: Local Event. Contact: Charlottesville Parks & Recreation. Contact Phone: 434-970-3260.
Wednesday, June 25, 2025, 3:00 PM – 7:00 PM.
Pen Park
1300 Pen Park Road
Charlottesville, VA 22901.
For more info visit www.charlottesville.gov. Scottsville’s Summer Concert Series
Fridays on the Canal is Scottsville’s new favorite way to kick off the weekend! Held on the fourth Friday of each month from May through September, this free summer concert series brings our riverside community together with live music, food trucks, wine & beer, and local vendors.
🎸 Free Admission
🍔 Family-Friendly
🕔 5–8 PM | Fourth Fridays | May–September.
Property: Omni Charlottesville Hotel. Event Type: Local Event.
Friday, June 27, 2025, 5:00 PM – 8:00 PM.
For more info visit fridaysonthecanal.com. Fridays After Five
Fridays After Five is Charlottesville’s signature free summer concert series, bringing the community together every Friday evening at Ting Pavilion on the Downtown Mall. Enjoy live performances from a diverse lineup of local and regional bands, spanning genres from rock and pop to soul, bluegrass, and more. Bring your friends and family, grab food and drinks from local vendors, and start your weekend with great music in a lively, family-friendly atmosphere. Rain or shine, it’s the place to be for music lovers and anyone looking for a fun, social Friday night out in the heart of Charlottesville.
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Art & Culture. Entertainment. Contact: Ting Pavilion. Contact Phone: (434) 245-4910.
Friday, June 27, 2025, 5:30 PM – 8:30 PM.
For more info visit www.tingpavilion.com. Charlottesville City Market
Charlottesville’s oldest open-air market is back! We offer a little bit of everything. Fresh fruits and veggies, handmade crafts, homemade baked goods, fresh roasted coffee, doughnuts, organic bagels, authentic cultural foods made on location, fresh artisan breads, and much more. You must visit the market; it is truly a taste of Charlottesville.
Event Type: Local Event. Event Category: Entertainment. Family. Holiday. Wellness & Fitness. Couples. Contact: Charlottesville Parks & Recreation. Contact Phone: 434-970-3260.
Saturday, June 28, 2025, 8:00 AM – 1:00 PM.
100 Water Street
Charlottesville, VA 22902.
For more info visit www.charlottesville.gov. Virginia Theatre Festival Presents- Into the Woods
Step into a magical world where classic fairy tales intertwine in Stephen Sondheim’s Tony Award-winning musical masterpiece, Into the Woods. Follow beloved characters like Cinderella, Little Red Riding Hood, and Jack (of beanstalk fame) as their stories collide in a journey that explores the true meaning of “happily ever after.” With an unforgettable score, witty lyrics, and enchanting storytelling, this production—directed and choreographed by Matthew Steffens—offers a fresh take on a modern classic. Perfect for families, musical lovers, and anyone who enjoys a touch of magic and adventure on stage.
Ticket Details:
Adult tickets: $40–$75 (varies by seat and performance)
Children 12 and under: $5 for all performances.
Event Type: Local Event. Event Category: Art & Culture. Contact: Culbreth Theatre. Contact Phone: (434) 924-3376.
Saturday, June 28, 2025, 2:00 PM – 5:00 PM.
109 Culbreth Rd, Charlottesville, VA 22903.
For more info visit virginiatheatrefestival.org. Fae Festival
Step into a realm of enchantment at the Fae Festival, Charlottesville’s urban Renaissance faire at IX Art Park! This magical weekend invites dreamers of all ages to don their finest fantasy attire and frolic through a bustling medieval market, revel to live minstrels and music, and feast on delights from local food vendors. Enjoy games, interactive performances, and marvels untold in a family-friendly celebration of the fantastical. Presented in partnership with the Virginia Tourism Corporation and Virginia Commission for the Arts, the Fae Festival blends Renaissance tradition with urban creativity for an unforgettable adventure.
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Art & Culture. Entertainment. Couples. Contact: IX Art Park. Contact Phone: (703) 209-4717.
Saturday, June 28, 2025, 3:00 PM – 9:00 PM.
For more info visit www.ixartpark.org. Rivanna Roots Concert Series
Rivanna Roots is a beloved family-friendly outdoor concert series held on the scenic banks of the Rivanna River. Enjoy an evening of outstanding local and regional music in a relaxed riverside setting. Bring your blanket or chair, savor local craft beer, cider, and wine from exclusive beverage partners, and enjoy delicious offerings from rotating food trucks. Kids 12 and under attend free (please add a free children’s ticket for attendance tracking).
Ticket Prices:
$15 in advance
$18 after 5:00 PM the day before the show and at the door
Kids 12 and under: Free (add free children’s ticket for tracking)
Season Pass: $195 full price (early bird $175 sold out) for all 13 concerts
Tickets support the performing artists and music education programs through The Front Porch Music School. Parking on-site is $5 cash per car; free parking options are available nearby. Dogs on leashes are welcome, and outside food is permitted (no outside alcohol). The event is rain or shine.
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Entertainment. Art & Culture. Couples. Contact: Rivanna River Company. Contact Phone: (434) 218-2052.
Saturday, June 28, 2025, 5:00 PM – 9:00 PM.
For more info visit frontporchcville.org. Virginia Theatre Festival Presents- Into the Woods
Step into a magical world where classic fairy tales intertwine in Stephen Sondheim’s Tony Award-winning musical masterpiece, Into the Woods. Follow beloved characters like Cinderella, Little Red Riding Hood, and Jack (of beanstalk fame) as their stories collide in a journey that explores the true meaning of “happily ever after.” With an unforgettable score, witty lyrics, and enchanting storytelling, this production—directed and choreographed by Matthew Steffens—offers a fresh take on a modern classic. Perfect for families, musical lovers, and anyone who enjoys a touch of magic and adventure on stage.
Ticket Details:
Adult tickets: $40–$75 (varies by seat and performance)
Children 12 and under: $5 for all performances.
Event Type: Local Event. Event Category: Art & Culture. Contact: Culbreth Theatre. Contact Phone: (434) 924-3376.
Saturday, June 28, 2025, 7:30 PM – 10:30 PM.
109 Culbreth Rd, Charlottesville, VA 22903.
For more info visit virginiatheatrefestival.org. Fae Festival
Step into a realm of enchantment at the Fae Festival, Charlottesville’s urban Renaissance faire at IX Art Park! This magical weekend invites dreamers of all ages to don their finest fantasy attire and frolic through a bustling medieval market, revel to live minstrels and music, and feast on delights from local food vendors. Enjoy games, interactive performances, and marvels untold in a family-friendly celebration of the fantastical. Presented in partnership with the Virginia Tourism Corporation and Virginia Commission for the Arts, the Fae Festival blends Renaissance tradition with urban creativity for an unforgettable adventure.
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Art & Culture. Entertainment. Couples. Contact: IX Art Park. Contact Phone: (703) 209-4717.
Sunday, June 29, 2025, 10:00 AM – 6:00 PM.
For more info visit www.ixartpark.org. King Family Vineyards (Roseland Polo Club)
Every Sunday from Memorial Day weekend (May 25, 2025) through mid-October (October 12, 2025), weather permitting
Regular match time: 12:00 PM (noon)
Gates open: 10:00 AM
Special summer schedule (July 6 – August 3, 2025): Matches at 5:00 PM and 6:30 PM; gates open at 4:00 PM
Experience the elegance and excitement of polo every Sunday at King Family Vineyards, set against the stunning backdrop of the Blue Ridge Mountains. Watch thrilling polo matches featuring skilled players and their magnificent ponies on the vineyard’s lush fields. Arrive early to enjoy tailgating with family and friends-set up your own space or reserve a spot with or without a tent for shade. Sip award-winning King Family wines, savor food from local vendors, and soak in the festive, welcoming atmosphere. The matches are perfect for all ages, whether you’re a polo enthusiast or new to the sport. During the hottest weeks in July, matches shift to cooler evening times to enhance your comfort. Reservations are recommended for tailgating spaces…
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Wellness & Fitness. Contact: King Family Vineyards. Contact Phone: (434) 823-7800.
Sunday, June 29, 2025, 10:00 AM – 2:00 PM.
For more info visit kingfamilyvineyards.com. Virginia Theatre Festival Presents- Into the Woods
Step into a magical world where classic fairy tales intertwine in Stephen Sondheim’s Tony Award-winning musical masterpiece, Into the Woods. Follow beloved characters like Cinderella, Little Red Riding Hood, and Jack (of beanstalk fame) as their stories collide in a journey that explores the true meaning of “happily ever after.” With an unforgettable score, witty lyrics, and enchanting storytelling, this production—directed and choreographed by Matthew Steffens—offers a fresh take on a modern classic. Perfect for families, musical lovers, and anyone who enjoys a touch of magic and adventure on stage.
Ticket Details:
Adult tickets: $40–$75 (varies by seat and performance)
Children 12 and under: $5 for all performances.
Event Type: Local Event. Event Category: Art & Culture. Contact: Culbreth Theatre. Contact Phone: (434) 924-3376.
Sunday, June 29, 2025, 2:00 PM – 5:00 PM.
109 Culbreth Rd, Charlottesville, VA 22903.
For more info visit virginiatheatrefestival.org. Virginia Theatre Festival Presents- Into the Woods
Step into a magical world where classic fairy tales intertwine in Stephen Sondheim’s Tony Award-winning musical masterpiece, Into the Woods. Follow beloved characters like Cinderella, Little Red Riding Hood, and Jack (of beanstalk fame) as their stories collide in a journey that explores the true meaning of “happily ever after.” With an unforgettable score, witty lyrics, and enchanting storytelling, this production—directed and choreographed by Matthew Steffens—offers a fresh take on a modern classic. Perfect for families, musical lovers, and anyone who enjoys a touch of magic and adventure on stage.
Ticket Details:
Adult tickets: $40–$75 (varies by seat and performance)
Children 12 and under: $5 for all performances.
Event Type: Local Event. Event Category: Art & Culture. Contact: Culbreth Theatre. Contact Phone: (434) 924-3376.
Tuesday, July 1, 2025, 7:30 PM – 10:30 PM.
109 Culbreth Rd, Charlottesville, VA 22903.
For more info visit virginiatheatrefestival.org. Farmers in the Park
Charlottesville’s oldest open-air market is back! We offer a little bit of everything. Fresh fruits and veggies, handmade crafts, homemade baked goods, fresh roasted coffee, doughnuts, organic bagels, authentic cultural foods made on location, fresh artisan breads, and much more. You must visit the market; it is truly a taste of Charlottesville.
Event Type: Local Event. Contact: Charlottesville Parks & Recreation. Contact Phone: 434-970-3260.
Wednesday, July 2, 2025, 3:00 PM – 7:00 PM.
Pen Park
1300 Pen Park Road
Charlottesville, VA 22901.
For more info visit www.charlottesville.gov. Virginia Theatre Festival Presents- Into the Woods
Step into a magical world where classic fairy tales intertwine in Stephen Sondheim’s Tony Award-winning musical masterpiece, Into the Woods. Follow beloved characters like Cinderella, Little Red Riding Hood, and Jack (of beanstalk fame) as their stories collide in a journey that explores the true meaning of “happily ever after.” With an unforgettable score, witty lyrics, and enchanting storytelling, this production—directed and choreographed by Matthew Steffens—offers a fresh take on a modern classic. Perfect for families, musical lovers, and anyone who enjoys a touch of magic and adventure on stage.
Ticket Details:
Adult tickets: $40–$75 (varies by seat and performance)
Children 12 and under: $5 for all performances.
Event Type: Local Event. Event Category: Art & Culture. Contact: Culbreth Theatre. Contact Phone: (434) 924-3376.
Wednesday, July 2, 2025, 7:30 PM – 10:30 PM.
109 Culbreth Rd, Charlottesville, VA 22903.
For more info visit virginiatheatrefestival.org. Virginia Theatre Festival Presents- Into the Woods
Step into a magical world where classic fairy tales intertwine in Stephen Sondheim’s Tony Award-winning musical masterpiece, Into the Woods. Follow beloved characters like Cinderella, Little Red Riding Hood, and Jack (of beanstalk fame) as their stories collide in a journey that explores the true meaning of “happily ever after.” With an unforgettable score, witty lyrics, and enchanting storytelling, this production—directed and choreographed by Matthew Steffens—offers a fresh take on a modern classic. Perfect for families, musical lovers, and anyone who enjoys a touch of magic and adventure on stage.
Ticket Details:
Adult tickets: $40–$75 (varies by seat and performance)
Children 12 and under: $5 for all performances.
Event Type: Local Event. Event Category: Art & Culture. Contact: Culbreth Theatre. Contact Phone: (434) 924-3376.
Thursday, July 3, 2025, 7:30 PM – 10:30 PM.
109 Culbreth Rd, Charlottesville, VA 22903.
For more info visit virginiatheatrefestival.org. Fridays After Five
Fridays After Five is Charlottesville’s signature free summer concert series, bringing the community together every Friday evening at Ting Pavilion on the Downtown Mall. Enjoy live performances from a diverse lineup of local and regional bands, spanning genres from rock and pop to soul, bluegrass, and more. Bring your friends and family, grab food and drinks from local vendors, and start your weekend with great music in a lively, family-friendly atmosphere. Rain or shine, it’s the place to be for music lovers and anyone looking for a fun, social Friday night out in the heart of Charlottesville.
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Art & Culture. Entertainment. Contact: Ting Pavilion. Contact Phone: (434) 245-4910.
Friday, July 4, 2025, 5:30 PM – 8:30 PM.
For more info visit www.tingpavilion.com. Charlottesville City Market
Charlottesville’s oldest open-air market is back! We offer a little bit of everything. Fresh fruits and veggies, handmade crafts, homemade baked goods, fresh roasted coffee, doughnuts, organic bagels, authentic cultural foods made on location, fresh artisan breads, and much more. You must visit the market; it is truly a taste of Charlottesville.
Event Type: Local Event. Event Category: Entertainment. Family. Holiday. Wellness & Fitness. Couples. Contact: Charlottesville Parks & Recreation. Contact Phone: 434-970-3260.
Saturday, July 5, 2025, 8:00 AM – 1:00 PM.
100 Water Street
Charlottesville, VA 22902.
For more info visit www.charlottesville.gov. Virginia Theatre Festival Presents- Into the Woods
Step into a magical world where classic fairy tales intertwine in Stephen Sondheim’s Tony Award-winning musical masterpiece, Into the Woods. Follow beloved characters like Cinderella, Little Red Riding Hood, and Jack (of beanstalk fame) as their stories collide in a journey that explores the true meaning of “happily ever after.” With an unforgettable score, witty lyrics, and enchanting storytelling, this production—directed and choreographed by Matthew Steffens—offers a fresh take on a modern classic. Perfect for families, musical lovers, and anyone who enjoys a touch of magic and adventure on stage.
Ticket Details:
Adult tickets: $40–$75 (varies by seat and performance)
Children 12 and under: $5 for all performances.
Event Type: Local Event. Event Category: Art & Culture. Contact: Culbreth Theatre. Contact Phone: (434) 924-3376.
Saturday, July 5, 2025, 2:00 PM – 5:00 PM.
109 Culbreth Rd, Charlottesville, VA 22903.
For more info visit virginiatheatrefestival.org. Virginia Theatre Festival Presents- Into the Woods
Step into a magical world where classic fairy tales intertwine in Stephen Sondheim’s Tony Award-winning musical masterpiece, Into the Woods. Follow beloved characters like Cinderella, Little Red Riding Hood, and Jack (of beanstalk fame) as their stories collide in a journey that explores the true meaning of “happily ever after.” With an unforgettable score, witty lyrics, and enchanting storytelling, this production—directed and choreographed by Matthew Steffens—offers a fresh take on a modern classic. Perfect for families, musical lovers, and anyone who enjoys a touch of magic and adventure on stage.
Ticket Details:
Adult tickets: $40–$75 (varies by seat and performance)
Children 12 and under: $5 for all performances.
Event Type: Local Event. Event Category: Art & Culture. Contact: Culbreth Theatre. Contact Phone: (434) 924-3376.
Saturday, July 5, 2025, 7:30 PM – 10:30 PM.
109 Culbreth Rd, Charlottesville, VA 22903.
For more info visit virginiatheatrefestival.org. Virginia Theatre Festival Presents- Into the Woods
Step into a magical world where classic fairy tales intertwine in Stephen Sondheim’s Tony Award-winning musical masterpiece, Into the Woods. Follow beloved characters like Cinderella, Little Red Riding Hood, and Jack (of beanstalk fame) as their stories collide in a journey that explores the true meaning of “happily ever after.” With an unforgettable score, witty lyrics, and enchanting storytelling, this production—directed and choreographed by Matthew Steffens—offers a fresh take on a modern classic. Perfect for families, musical lovers, and anyone who enjoys a touch of magic and adventure on stage.
Ticket Details:
Adult tickets: $40–$75 (varies by seat and performance)
Children 12 and under: $5 for all performances.
Event Type: Local Event. Event Category: Art & Culture. Contact: Culbreth Theatre. Contact Phone: (434) 924-3376.
Sunday, July 6, 2025, 2:00 PM – 5:00 PM.
109 Culbreth Rd, Charlottesville, VA 22903.
For more info visit virginiatheatrefestival.org. King Family Vineyards (Roseland Polo Club)
Every Sunday from Memorial Day weekend (May 25, 2025) through mid-October (October 12, 2025), weather permitting
Regular match time: 12:00 PM (noon)
Gates open: 10:00 AM
Special summer schedule (July 6 – August 3, 2025): Matches at 5:00 PM and 6:30 PM; gates open at 4:00 PM
Experience the elegance and excitement of polo every Sunday at King Family Vineyards, set against the stunning backdrop of the Blue Ridge Mountains. Watch thrilling polo matches featuring skilled players and their magnificent ponies on the vineyard’s lush fields. Arrive early to enjoy tailgating with family and friends-set up your own space or reserve a spot with or without a tent for shade. Sip award-winning King Family wines, savor food from local vendors, and soak in the festive, welcoming atmosphere. The matches are perfect for all ages, whether you’re a polo enthusiast or new to the sport. During the hottest weeks in July, matches shift to cooler evening times to enhance your comfort. Reservations are recommended for tailgating spaces…
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Wellness & Fitness. Contact: King Family Vineyards. Contact Phone: (434) 823-7800.
Sunday, July 6, 2025, 4:00 PM – 8:00 PM.
For more info visit kingfamilyvineyards.com. Farmers in the Park
Charlottesville’s oldest open-air market is back! We offer a little bit of everything. Fresh fruits and veggies, handmade crafts, homemade baked goods, fresh roasted coffee, doughnuts, organic bagels, authentic cultural foods made on location, fresh artisan breads, and much more. You must visit the market; it is truly a taste of Charlottesville.
Event Type: Local Event. Contact: Charlottesville Parks & Recreation. Contact Phone: 434-970-3260.
Wednesday, July 9, 2025, 3:00 PM – 7:00 PM.
Pen Park
1300 Pen Park Road
Charlottesville, VA 22901.
For more info visit www.charlottesville.gov. Fridays After Five
Fridays After Five is Charlottesville’s signature free summer concert series, bringing the community together every Friday evening at Ting Pavilion on the Downtown Mall. Enjoy live performances from a diverse lineup of local and regional bands, spanning genres from rock and pop to soul, bluegrass, and more. Bring your friends and family, grab food and drinks from local vendors, and start your weekend with great music in a lively, family-friendly atmosphere. Rain or shine, it’s the place to be for music lovers and anyone looking for a fun, social Friday night out in the heart of Charlottesville.
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Art & Culture. Entertainment. Contact: Ting Pavilion. Contact Phone: (434) 245-4910.
Friday, July 11, 2025, 5:30 PM – 8:30 PM.
For more info visit www.tingpavilion.com. Charlottesville Opera Presents: The Pirates of Penzance
Set sail for laughter and adventure with Gilbert & Sullivan’s comic masterpiece, The Pirates of Penzance! This witty and whimsical operetta tells the tale of Frederic, a young apprentice pirate, who falls in love with the beautiful Mabel and tries to escape the clutches of his bumbling pirate crew. Bursting with clever lyrics, catchy tunes, and hilarious hijinks, this production by Charlottesville Opera promises fun for all ages. Performed with full orchestra and a talented cast, it’s the perfect summer treat for families, opera fans, and anyone looking for a joyous night at the theater.
Student/Youth: $15
General Admission: $30, $45, $65, $85 (tiered seating/pricing).
Event Type: Local Event. Event Category: Art & Culture. Couples. Entertainment. Contact: The Paramount Theater. Contact Phone: (434) 979-1333.
Friday, July 11, 2025, 7:00 PM – 9:30 PM.
215 E Main St, Charlottesville, VA 22902.
For more info visit charlottesville.theparamount.net. Virginia Theatre Festival Presents- The Heart Sellers
Pulitzer Prize finalist Lloyd Suh’s The Heart Sellers is a sweet, funny, and deeply moving play that highlights the experiences of two 20-something immigrant women, one from the Philippines and one from South Korea, who meet by chance in a grocery store on Thanksgiving night in 1973. Set eight years after the Hart–Celler Act abolished immigration quotas in America, the play follows Luna and Jane as they bond over their longing for home and excitement for the future. Over the course of one evening, they share hopes, fears, dreams, and laughter, illuminating the immigrant experience and asking, “Would you give up your heart to make a new home?” Directed by Desdemona Chiang, this heartfelt story is filled with humor, humanity, and resonance for today’s audiences.
Ticket Details:
Adult tickets: $40–$75 (varies by seat and performance)
Children 12 and under: $5 for all performances
Note: No late seating due to the intimate size of Helms Theatre.
Event Type: Local Event. Event Category: Art & Culture. Contact: Helms Theatre. Contact Phone: (434) 924-3376.
Friday, July 11, 2025, 7:30 PM – 9:00 PM.
109 Culbreth Rd, Charlottesville, VA 22903.
For more info visit virginiatheatrefestival.org. Charlottesville City Market
Charlottesville’s oldest open-air market is back! We offer a little bit of everything. Fresh fruits and veggies, handmade crafts, homemade baked goods, fresh roasted coffee, doughnuts, organic bagels, authentic cultural foods made on location, fresh artisan breads, and much more. You must visit the market; it is truly a taste of Charlottesville.
Event Type: Local Event. Event Category: Entertainment. Family. Holiday. Wellness & Fitness. Couples. Contact: Charlottesville Parks & Recreation. Contact Phone: 434-970-3260.
Saturday, July 12, 2025, 8:00 AM – 1:00 PM.
100 Water Street
Charlottesville, VA 22902.
For more info visit www.charlottesville.gov. Charlottesville Opera Presents: The Pirates of Penzance
Set sail for laughter and adventure with Gilbert & Sullivan’s comic masterpiece, The Pirates of Penzance! This witty and whimsical operetta tells the tale of Frederic, a young apprentice pirate, who falls in love with the beautiful Mabel and tries to escape the clutches of his bumbling pirate crew. Bursting with clever lyrics, catchy tunes, and hilarious hijinks, this production by Charlottesville Opera promises fun for all ages. Performed with full orchestra and a talented cast, it’s the perfect summer treat for families, opera fans, and anyone looking for a joyous night at the theater.
Student/Youth: $15
General Admission: $30, $45, $65, $85 (tiered seating/pricing).
Event Type: Local Event. Event Category: Art & Culture. Couples. Entertainment. Contact: The Paramount Theater. Contact Phone: (434) 979-1333.
Saturday, July 12, 2025, 2:00 PM – 4:30 PM.
215 E Main St, Charlottesville, VA 22902.
For more info visit charlottesville.theparamount.net. Rivanna Roots Concert Series
Rivanna Roots is a beloved family-friendly outdoor concert series held on the scenic banks of the Rivanna River. Enjoy an evening of outstanding local and regional music in a relaxed riverside setting. Bring your blanket or chair, savor local craft beer, cider, and wine from exclusive beverage partners, and enjoy delicious offerings from rotating food trucks. Kids 12 and under attend free (please add a free children’s ticket for attendance tracking).
Ticket Prices:
$15 in advance
$18 after 5:00 PM the day before the show and at the door
Kids 12 and under: Free (add free children’s ticket for tracking)
Season Pass: $195 full price (early bird $175 sold out) for all 13 concerts
Tickets support the performing artists and music education programs through The Front Porch Music School. Parking on-site is $5 cash per car; free parking options are available nearby. Dogs on leashes are welcome, and outside food is permitted (no outside alcohol). The event is rain or shine.
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Entertainment. Art & Culture. Couples. Contact: Rivanna River Company. Contact Phone: (434) 218-2052.
Saturday, July 12, 2025, 5:00 PM – 9:00 PM.
For more info visit frontporchcville.org. Virginia Theatre Festival Presents- The Heart Sellers
Pulitzer Prize finalist Lloyd Suh’s The Heart Sellers is a sweet, funny, and deeply moving play that highlights the experiences of two 20-something immigrant women, one from the Philippines and one from South Korea, who meet by chance in a grocery store on Thanksgiving night in 1973. Set eight years after the Hart–Celler Act abolished immigration quotas in America, the play follows Luna and Jane as they bond over their longing for home and excitement for the future. Over the course of one evening, they share hopes, fears, dreams, and laughter, illuminating the immigrant experience and asking, “Would you give up your heart to make a new home?” Directed by Desdemona Chiang, this heartfelt story is filled with humor, humanity, and resonance for today’s audiences.
Ticket Details:
Adult tickets: $40–$75 (varies by seat and performance)
Children 12 and under: $5 for all performances
Note: No late seating due to the intimate size of Helms Theatre.
Event Type: Local Event. Event Category: Art & Culture. Contact: Helms Theatre. Contact Phone: (434) 924-3376.
Saturday, July 12, 2025, 7:30 PM – 9:00 PM.
109 Culbreth Rd, Charlottesville, VA 22903.
For more info visit virginiatheatrefestival.org. Charlottesville Opera Presents: The Pirates of Penzance
Set sail for laughter and adventure with Gilbert & Sullivan’s comic masterpiece, The Pirates of Penzance! This witty and whimsical operetta tells the tale of Frederic, a young apprentice pirate, who falls in love with the beautiful Mabel and tries to escape the clutches of his bumbling pirate crew. Bursting with clever lyrics, catchy tunes, and hilarious hijinks, this production by Charlottesville Opera promises fun for all ages. Performed with full orchestra and a talented cast, it’s the perfect summer treat for families, opera fans, and anyone looking for a joyous night at the theater.
Student/Youth: $15
General Admission: $30, $45, $65, $85 (tiered seating/pricing).
Event Type: Local Event. Event Category: Art & Culture. Couples. Entertainment. Contact: The Paramount Theater. Contact Phone: (434) 979-1333.
Sunday, July 13, 2025, 2:00 PM – 4:30 PM.
215 E Main St, Charlottesville, VA 22902.
For more info visit charlottesville.theparamount.net. Virginia Theatre Festival Presents- The Heart Sellers
Pulitzer Prize finalist Lloyd Suh’s The Heart Sellers is a sweet, funny, and deeply moving play that highlights the experiences of two 20-something immigrant women, one from the Philippines and one from South Korea, who meet by chance in a grocery store on Thanksgiving night in 1973. Set eight years after the Hart–Celler Act abolished immigration quotas in America, the play follows Luna and Jane as they bond over their longing for home and excitement for the future. Over the course of one evening, they share hopes, fears, dreams, and laughter, illuminating the immigrant experience and asking, “Would you give up your heart to make a new home?” Directed by Desdemona Chiang, this heartfelt story is filled with humor, humanity, and resonance for today’s audiences.
Ticket Details:
Adult tickets: $40–$75 (varies by seat and performance)
Children 12 and under: $5 for all performances
Note: No late seating due to the intimate size of Helms Theatre.
Event Type: Local Event. Event Category: Art & Culture. Contact: Helms Theatre. Contact Phone: (434) 924-3376.
Sunday, July 13, 2025, 2:00 PM – 3:30 PM.
109 Culbreth Rd, Charlottesville, VA 22903.
For more info visit virginiatheatrefestival.org. King Family Vineyards (Roseland Polo Club)
Every Sunday from Memorial Day weekend (May 25, 2025) through mid-October (October 12, 2025), weather permitting
Regular match time: 12:00 PM (noon)
Gates open: 10:00 AM
Special summer schedule (July 6 – August 3, 2025): Matches at 5:00 PM and 6:30 PM; gates open at 4:00 PM
Experience the elegance and excitement of polo every Sunday at King Family Vineyards, set against the stunning backdrop of the Blue Ridge Mountains. Watch thrilling polo matches featuring skilled players and their magnificent ponies on the vineyard’s lush fields. Arrive early to enjoy tailgating with family and friends-set up your own space or reserve a spot with or without a tent for shade. Sip award-winning King Family wines, savor food from local vendors, and soak in the festive, welcoming atmosphere. The matches are perfect for all ages, whether you’re a polo enthusiast or new to the sport. During the hottest weeks in July, matches shift to cooler evening times to enhance your comfort. Reservations are recommended for tailgating spaces…
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Wellness & Fitness. Contact: King Family Vineyards. Contact Phone: (434) 823-7800.
Sunday, July 13, 2025, 4:00 PM – 8:00 PM.
For more info visit kingfamilyvineyards.com. Virginia Theatre Festival Presents- The Heart Sellers
Pulitzer Prize finalist Lloyd Suh’s The Heart Sellers is a sweet, funny, and deeply moving play that highlights the experiences of two 20-something immigrant women, one from the Philippines and one from South Korea, who meet by chance in a grocery store on Thanksgiving night in 1973. Set eight years after the Hart–Celler Act abolished immigration quotas in America, the play follows Luna and Jane as they bond over their longing for home and excitement for the future. Over the course of one evening, they share hopes, fears, dreams, and laughter, illuminating the immigrant experience and asking, “Would you give up your heart to make a new home?” Directed by Desdemona Chiang, this heartfelt story is filled with humor, humanity, and resonance for today’s audiences.
Ticket Details:
Adult tickets: $40–$75 (varies by seat and performance)
Children 12 and under: $5 for all performances
Note: No late seating due to the intimate size of Helms Theatre.
Event Type: Local Event. Event Category: Art & Culture. Contact: Helms Theatre. Contact Phone: (434) 924-3376.
Tuesday, July 15, 2025, 7:30 PM – 9:00 PM.
109 Culbreth Rd, Charlottesville, VA 22903.
For more info visit virginiatheatrefestival.org. Farmers in the Park
Charlottesville’s oldest open-air market is back! We offer a little bit of everything. Fresh fruits and veggies, handmade crafts, homemade baked goods, fresh roasted coffee, doughnuts, organic bagels, authentic cultural foods made on location, fresh artisan breads, and much more. You must visit the market; it is truly a taste of Charlottesville.
Event Type: Local Event. Contact: Charlottesville Parks & Recreation. Contact Phone: 434-970-3260.
Wednesday, July 16, 2025, 3:00 PM – 7:00 PM.
Pen Park
1300 Pen Park Road
Charlottesville, VA 22901.
For more info visit www.charlottesville.gov. Virginia Theatre Festival Presents- The Heart Sellers
Pulitzer Prize finalist Lloyd Suh’s The Heart Sellers is a sweet, funny, and deeply moving play that highlights the experiences of two 20-something immigrant women, one from the Philippines and one from South Korea, who meet by chance in a grocery store on Thanksgiving night in 1973. Set eight years after the Hart–Celler Act abolished immigration quotas in America, the play follows Luna and Jane as they bond over their longing for home and excitement for the future. Over the course of one evening, they share hopes, fears, dreams, and laughter, illuminating the immigrant experience and asking, “Would you give up your heart to make a new home?” Directed by Desdemona Chiang, this heartfelt story is filled with humor, humanity, and resonance for today’s audiences.
Ticket Details:
Adult tickets: $40–$75 (varies by seat and performance)
Children 12 and under: $5 for all performances
Note: No late seating due to the intimate size of Helms Theatre.
Event Type: Local Event. Event Category: Art & Culture. Contact: Helms Theatre. Contact Phone: (434) 924-3376.
Wednesday, July 16, 2025, 7:30 PM – 9:00 PM.
109 Culbreth Rd, Charlottesville, VA 22903.
For more info visit virginiatheatrefestival.org. Virginia Theatre Festival Presents- The Heart Sellers
Pulitzer Prize finalist Lloyd Suh’s The Heart Sellers is a sweet, funny, and deeply moving play that highlights the experiences of two 20-something immigrant women, one from the Philippines and one from South Korea, who meet by chance in a grocery store on Thanksgiving night in 1973. Set eight years after the Hart–Celler Act abolished immigration quotas in America, the play follows Luna and Jane as they bond over their longing for home and excitement for the future. Over the course of one evening, they share hopes, fears, dreams, and laughter, illuminating the immigrant experience and asking, “Would you give up your heart to make a new home?” Directed by Desdemona Chiang, this heartfelt story is filled with humor, humanity, and resonance for today’s audiences.
Ticket Details:
Adult tickets: $40–$75 (varies by seat and performance)
Children 12 and under: $5 for all performances
Note: No late seating due to the intimate size of Helms Theatre.
Event Type: Local Event. Event Category: Art & Culture. Contact: Helms Theatre. Contact Phone: (434) 924-3376.
Thursday, July 17, 2025, 7:30 PM – 9:00 PM.
109 Culbreth Rd, Charlottesville, VA 22903.
For more info visit virginiatheatrefestival.org. The Basketball Tournament (TBT) 2025 – Charlottesville Regional
The Basketball Tournament (TBT) returns to Charlottesville for the 2025 regional, hosted at John Paul Jones Arena! This single-elimination, winner-take-all tournament features top talent and a $1 million prize for the champion. The regional will be headlined by “Embrace The Pace,” a UVA alumni team led by Virginia legend Kyle Guy. Thanks to TBT’s new Home Court Advantage Model, the UVA alumni could potentially play all the way through the championship on their home court.
Fans can expect high-energy games, exciting upsets, and a chance to cheer on former UVA stars as they compete for glory. The event is family-friendly, with clear bag and mobile entry policies in effect. Don’t miss this unique opportunity to see elite basketball and support your favorite Hoos!
Event Type: Local Event. Contact: John Paul Jones Arena. Contact Phone: (434) 243-4960.
Friday, July 18, 2025 – Wednesday, July 23, 2025.
295 Massie Rd, Charlottesville, VA 22903.
For more info visit www.johnpauljonesarena.com. Fridays After Five
Fridays After Five is Charlottesville’s signature free summer concert series, bringing the community together every Friday evening at Ting Pavilion on the Downtown Mall. Enjoy live performances from a diverse lineup of local and regional bands, spanning genres from rock and pop to soul, bluegrass, and more. Bring your friends and family, grab food and drinks from local vendors, and start your weekend with great music in a lively, family-friendly atmosphere. Rain or shine, it’s the place to be for music lovers and anyone looking for a fun, social Friday night out in the heart of Charlottesville.
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Art & Culture. Entertainment. Contact: Ting Pavilion. Contact Phone: (434) 245-4910.
Friday, July 18, 2025, 5:30 PM – 8:30 PM.
For more info visit www.tingpavilion.com. Virginia Theatre Festival Presents- The Heart Sellers
Pulitzer Prize finalist Lloyd Suh’s The Heart Sellers is a sweet, funny, and deeply moving play that highlights the experiences of two 20-something immigrant women, one from the Philippines and one from South Korea, who meet by chance in a grocery store on Thanksgiving night in 1973. Set eight years after the Hart–Celler Act abolished immigration quotas in America, the play follows Luna and Jane as they bond over their longing for home and excitement for the future. Over the course of one evening, they share hopes, fears, dreams, and laughter, illuminating the immigrant experience and asking, “Would you give up your heart to make a new home?” Directed by Desdemona Chiang, this heartfelt story is filled with humor, humanity, and resonance for today’s audiences.
Ticket Details:
Adult tickets: $40–$75 (varies by seat and performance)
Children 12 and under: $5 for all performances
Note: No late seating due to the intimate size of Helms Theatre.
Event Type: Local Event. Event Category: Art & Culture. Contact: Helms Theatre. Contact Phone: (434) 924-3376.
Friday, July 18, 2025, 7:30 PM – 9:00 PM.
109 Culbreth Rd, Charlottesville, VA 22903.
For more info visit virginiatheatrefestival.org. Charlottesville City Market
Charlottesville’s oldest open-air market is back! We offer a little bit of everything. Fresh fruits and veggies, handmade crafts, homemade baked goods, fresh roasted coffee, doughnuts, organic bagels, authentic cultural foods made on location, fresh artisan breads, and much more. You must visit the market; it is truly a taste of Charlottesville.
Event Type: Local Event. Event Category: Entertainment. Family. Holiday. Wellness & Fitness. Couples. Contact: Charlottesville Parks & Recreation. Contact Phone: 434-970-3260.
Saturday, July 19, 2025, 8:00 AM – 1:00 PM.
100 Water Street
Charlottesville, VA 22902.
For more info visit www.charlottesville.gov. Virginia Theatre Festival Presents- The Heart Sellers
Pulitzer Prize finalist Lloyd Suh’s The Heart Sellers is a sweet, funny, and deeply moving play that highlights the experiences of two 20-something immigrant women, one from the Philippines and one from South Korea, who meet by chance in a grocery store on Thanksgiving night in 1973. Set eight years after the Hart–Celler Act abolished immigration quotas in America, the play follows Luna and Jane as they bond over their longing for home and excitement for the future. Over the course of one evening, they share hopes, fears, dreams, and laughter, illuminating the immigrant experience and asking, “Would you give up your heart to make a new home?” Directed by Desdemona Chiang, this heartfelt story is filled with humor, humanity, and resonance for today’s audiences.
Ticket Details:
Adult tickets: $40–$75 (varies by seat and performance)
Children 12 and under: $5 for all performances
Note: No late seating due to the intimate size of Helms Theatre.
Event Type: Local Event. Event Category: Art & Culture. Contact: Helms Theatre. Contact Phone: (434) 924-3376.
Saturday, July 19, 2025, 2:00 PM – 3:30 PM.
109 Culbreth Rd, Charlottesville, VA 22903.
For more info visit virginiatheatrefestival.org. Virginia Theatre Festival Presents- The Heart Sellers
Pulitzer Prize finalist Lloyd Suh’s The Heart Sellers is a sweet, funny, and deeply moving play that highlights the experiences of two 20-something immigrant women, one from the Philippines and one from South Korea, who meet by chance in a grocery store on Thanksgiving night in 1973. Set eight years after the Hart–Celler Act abolished immigration quotas in America, the play follows Luna and Jane as they bond over their longing for home and excitement for the future. Over the course of one evening, they share hopes, fears, dreams, and laughter, illuminating the immigrant experience and asking, “Would you give up your heart to make a new home?” Directed by Desdemona Chiang, this heartfelt story is filled with humor, humanity, and resonance for today’s audiences.
Ticket Details:
Adult tickets: $40–$75 (varies by seat and performance)
Children 12 and under: $5 for all performances
Note: No late seating due to the intimate size of Helms Theatre.
Event Type: Local Event. Event Category: Art & Culture. Contact: Helms Theatre. Contact Phone: (434) 924-3376.
Saturday, July 19, 2025, 7:30 PM – 9:00 PM.
109 Culbreth Rd, Charlottesville, VA 22903.
For more info visit virginiatheatrefestival.org. Virginia Theatre Festival Presents- The Heart Sellers
Pulitzer Prize finalist Lloyd Suh’s The Heart Sellers is a sweet, funny, and deeply moving play that highlights the experiences of two 20-something immigrant women, one from the Philippines and one from South Korea, who meet by chance in a grocery store on Thanksgiving night in 1973. Set eight years after the Hart–Celler Act abolished immigration quotas in America, the play follows Luna and Jane as they bond over their longing for home and excitement for the future. Over the course of one evening, they share hopes, fears, dreams, and laughter, illuminating the immigrant experience and asking, “Would you give up your heart to make a new home?” Directed by Desdemona Chiang, this heartfelt story is filled with humor, humanity, and resonance for today’s audiences.
Ticket Details:
Adult tickets: $40–$75 (varies by seat and performance)
Children 12 and under: $5 for all performances
Note: No late seating due to the intimate size of Helms Theatre.
Event Type: Local Event. Event Category: Art & Culture. Contact: Helms Theatre. Contact Phone: (434) 924-3376.
Sunday, July 20, 2025, 2:00 PM – 3:30 PM.
109 Culbreth Rd, Charlottesville, VA 22903.
For more info visit virginiatheatrefestival.org. King Family Vineyards (Roseland Polo Club)
Every Sunday from Memorial Day weekend (May 25, 2025) through mid-October (October 12, 2025), weather permitting
Regular match time: 12:00 PM (noon)
Gates open: 10:00 AM
Special summer schedule (July 6 – August 3, 2025): Matches at 5:00 PM and 6:30 PM; gates open at 4:00 PM
Experience the elegance and excitement of polo every Sunday at King Family Vineyards, set against the stunning backdrop of the Blue Ridge Mountains. Watch thrilling polo matches featuring skilled players and their magnificent ponies on the vineyard’s lush fields. Arrive early to enjoy tailgating with family and friends-set up your own space or reserve a spot with or without a tent for shade. Sip award-winning King Family wines, savor food from local vendors, and soak in the festive, welcoming atmosphere. The matches are perfect for all ages, whether you’re a polo enthusiast or new to the sport. During the hottest weeks in July, matches shift to cooler evening times to enhance your comfort. Reservations are recommended for tailgating spaces…
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Wellness & Fitness. Contact: King Family Vineyards. Contact Phone: (434) 823-7800.
Sunday, July 20, 2025, 4:00 PM – 8:00 PM.
For more info visit kingfamilyvineyards.com. Charlottesville Restaurant Week
Charlottesville Restaurant Week is a highly anticipated annual event celebrating the city’s vibrant culinary scene. For one week, dozens of top local restaurants offer special three-course prix-fixe dinners at set price points of $25, $35, or $45 per person (excluding tax, tip, and beverages). Diners can explore new restaurants or revisit favorites, sampling creative menus crafted just for Restaurant Week. Participating venues span all major neighborhoods, making it easy to find a great meal close to home or work. Menus for each restaurant are available online—simply click on a restaurant’s logo to view their offerings. Reservations are strongly recommended, as this is a popular event and tables fill quickly.
Ticket Details:
No advance tickets required
Choose your restaurant, review their special menu, and make a reservation directly with the venue.
Property: Omni Charlottesville Hotel. Event Type: Local Event. Contact: Multiple participating restaurants across Charlottesville.
Monday, July 21, 2025 – Sunday, July 27, 2025.
For more info visit www.c-villerestaurantweek.com. Farmers in the Park
Charlottesville’s oldest open-air market is back! We offer a little bit of everything. Fresh fruits and veggies, handmade crafts, homemade baked goods, fresh roasted coffee, doughnuts, organic bagels, authentic cultural foods made on location, fresh artisan breads, and much more. You must visit the market; it is truly a taste of Charlottesville.
Event Type: Local Event. Contact: Charlottesville Parks & Recreation. Contact Phone: 434-970-3260.
Wednesday, July 23, 2025, 3:00 PM – 7:00 PM.
Pen Park
1300 Pen Park Road
Charlottesville, VA 22901.
For more info visit www.charlottesville.gov. Virginia Theatre Festival Presents- Get Happy!
Get Happy! is a dynamic and electric evening celebrating the music and legacy of American icon Judy Garland, performed by acclaimed cabaret artist and UVA alumna Jenna Pastuszek. Rather than imitation, Pastuszek weaves her own story with Garland’s, blending her formidable vocal talents with the allure of timeless standards and hidden gems from the Judy Garland songbook. Audiences will be taken “over the rainbow and then some” in this joyful, heartfelt, and entertaining tribute to one of the world’s greatest entertainers. Perfect for musical lovers and anyone seeking an uplifting night at the theater.
Ticket Details:
Adult tickets: $40–$75 (varies by seat and performance)
Children 12 and under: $5 for all performances.
Event Type: Local Event. Event Category: Art & Culture. Contact: Ruth Caplin Theatre. Contact Phone: (434) 924-3376.
Thursday, July 24, 2025, 7:30 PM – 9:00 PM.
109 Culbreth Rd, Charlottesville, VA 22903.
For more info visit virginiatheatrefestival.org. Scottsville’s Summer Concert Series
Fridays on the Canal is Scottsville’s new favorite way to kick off the weekend! Held on the fourth Friday of each month from May through September, this free summer concert series brings our riverside community together with live music, food trucks, wine & beer, and local vendors.
🎸 Free Admission
🍔 Family-Friendly
🕔 5–8 PM | Fourth Fridays | May–September.
Property: Omni Charlottesville Hotel. Event Type: Local Event.
Friday, July 25, 2025, 5:00 PM – 8:00 PM.
For more info visit fridaysonthecanal.com. Fridays After Five
Fridays After Five is Charlottesville’s signature free summer concert series, bringing the community together every Friday evening at Ting Pavilion on the Downtown Mall. Enjoy live performances from a diverse lineup of local and regional bands, spanning genres from rock and pop to soul, bluegrass, and more. Bring your friends and family, grab food and drinks from local vendors, and start your weekend with great music in a lively, family-friendly atmosphere. Rain or shine, it’s the place to be for music lovers and anyone looking for a fun, social Friday night out in the heart of Charlottesville.
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Art & Culture. Entertainment. Contact: Ting Pavilion. Contact Phone: (434) 245-4910.
Friday, July 25, 2025, 5:30 PM – 8:30 PM.
For more info visit www.tingpavilion.com. Virginia Theatre Festival Presents- Get Happy!
Get Happy! is a dynamic and electric evening celebrating the music and legacy of American icon Judy Garland, performed by acclaimed cabaret artist and UVA alumna Jenna Pastuszek. Rather than imitation, Pastuszek weaves her own story with Garland’s, blending her formidable vocal talents with the allure of timeless standards and hidden gems from the Judy Garland songbook. Audiences will be taken “over the rainbow and then some” in this joyful, heartfelt, and entertaining tribute to one of the world’s greatest entertainers. Perfect for musical lovers and anyone seeking an uplifting night at the theater.
Ticket Details:
Adult tickets: $40–$75 (varies by seat and performance)
Children 12 and under: $5 for all performances.
Event Type: Local Event. Event Category: Art & Culture. Contact: Ruth Caplin Theatre. Contact Phone: (434) 924-3376.
Friday, July 25, 2025, 7:30 PM – 9:00 PM.
109 Culbreth Rd, Charlottesville, VA 22903.
For more info visit virginiatheatrefestival.org. Charlottesville City Market
Charlottesville’s oldest open-air market is back! We offer a little bit of everything. Fresh fruits and veggies, handmade crafts, homemade baked goods, fresh roasted coffee, doughnuts, organic bagels, authentic cultural foods made on location, fresh artisan breads, and much more. You must visit the market; it is truly a taste of Charlottesville.
Event Type: Local Event. Event Category: Entertainment. Family. Holiday. Wellness & Fitness. Couples. Contact: Charlottesville Parks & Recreation. Contact Phone: 434-970-3260.
Saturday, July 26, 2025, 8:00 AM – 1:00 PM.
100 Water Street
Charlottesville, VA 22902.
For more info visit www.charlottesville.gov. Virginia Theatre Festival Presents- Get Happy!
Get Happy! is a dynamic and electric evening celebrating the music and legacy of American icon Judy Garland, performed by acclaimed cabaret artist and UVA alumna Jenna Pastuszek. Rather than imitation, Pastuszek weaves her own story with Garland’s, blending her formidable vocal talents with the allure of timeless standards and hidden gems from the Judy Garland songbook. Audiences will be taken “over the rainbow and then some” in this joyful, heartfelt, and entertaining tribute to one of the world’s greatest entertainers. Perfect for musical lovers and anyone seeking an uplifting night at the theater.
Ticket Details:
Adult tickets: $40–$75 (varies by seat and performance)
Children 12 and under: $5 for all performances.
Event Type: Local Event. Event Category: Art & Culture. Contact: Ruth Caplin Theatre. Contact Phone: (434) 924-3376.
Saturday, July 26, 2025, 2:00 PM – 3:30 PM.
109 Culbreth Rd, Charlottesville, VA 22903.
For more info visit virginiatheatrefestival.org. Rivanna Roots Concert Series
Rivanna Roots is a beloved family-friendly outdoor concert series held on the scenic banks of the Rivanna River. Enjoy an evening of outstanding local and regional music in a relaxed riverside setting. Bring your blanket or chair, savor local craft beer, cider, and wine from exclusive beverage partners, and enjoy delicious offerings from rotating food trucks. Kids 12 and under attend free (please add a free children’s ticket for attendance tracking).
Ticket Prices:
$15 in advance
$18 after 5:00 PM the day before the show and at the door
Kids 12 and under: Free (add free children’s ticket for tracking)
Season Pass: $195 full price (early bird $175 sold out) for all 13 concerts
Tickets support the performing artists and music education programs through The Front Porch Music School. Parking on-site is $5 cash per car; free parking options are available nearby. Dogs on leashes are welcome, and outside food is permitted (no outside alcohol). The event is rain or shine.
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Entertainment. Art & Culture. Couples. Contact: Rivanna River Company. Contact Phone: (434) 218-2052.
Saturday, July 26, 2025, 5:00 PM – 9:00 PM.
For more info visit frontporchcville.org. Virginia Theatre Festival Presents- Get Happy!
Get Happy! is a dynamic and electric evening celebrating the music and legacy of American icon Judy Garland, performed by acclaimed cabaret artist and UVA alumna Jenna Pastuszek. Rather than imitation, Pastuszek weaves her own story with Garland’s, blending her formidable vocal talents with the allure of timeless standards and hidden gems from the Judy Garland songbook. Audiences will be taken “over the rainbow and then some” in this joyful, heartfelt, and entertaining tribute to one of the world’s greatest entertainers. Perfect for musical lovers and anyone seeking an uplifting night at the theater.
Ticket Details:
Adult tickets: $40–$75 (varies by seat and performance)
Children 12 and under: $5 for all performances.
Event Type: Local Event. Event Category: Art & Culture. Contact: Ruth Caplin Theatre. Contact Phone: (434) 924-3376.
Saturday, July 26, 2025, 7:30 PM – 9:00 PM.
109 Culbreth Rd, Charlottesville, VA 22903.
For more info visit virginiatheatrefestival.org. Virginia Theatre Festival Presents- Get Happy!
Get Happy! is a dynamic and electric evening celebrating the music and legacy of American icon Judy Garland, performed by acclaimed cabaret artist and UVA alumna Jenna Pastuszek. Rather than imitation, Pastuszek weaves her own story with Garland’s, blending her formidable vocal talents with the allure of timeless standards and hidden gems from the Judy Garland songbook. Audiences will be taken “over the rainbow and then some” in this joyful, heartfelt, and entertaining tribute to one of the world’s greatest entertainers. Perfect for musical lovers and anyone seeking an uplifting night at the theater.
Ticket Details:
Adult tickets: $40–$75 (varies by seat and performance)
Children 12 and under: $5 for all performances.
Event Type: Local Event. Event Category: Art & Culture. Contact: Ruth Caplin Theatre. Contact Phone: (434) 924-3376.
Sunday, July 27, 2025, 2:00 PM – 3:30 PM.
109 Culbreth Rd, Charlottesville, VA 22903.
For more info visit virginiatheatrefestival.org. King Family Vineyards (Roseland Polo Club)
Every Sunday from Memorial Day weekend (May 25, 2025) through mid-October (October 12, 2025), weather permitting
Regular match time: 12:00 PM (noon)
Gates open: 10:00 AM
Special summer schedule (July 6 – August 3, 2025): Matches at 5:00 PM and 6:30 PM; gates open at 4:00 PM
Experience the elegance and excitement of polo every Sunday at King Family Vineyards, set against the stunning backdrop of the Blue Ridge Mountains. Watch thrilling polo matches featuring skilled players and their magnificent ponies on the vineyard’s lush fields. Arrive early to enjoy tailgating with family and friends-set up your own space or reserve a spot with or without a tent for shade. Sip award-winning King Family wines, savor food from local vendors, and soak in the festive, welcoming atmosphere. The matches are perfect for all ages, whether you’re a polo enthusiast or new to the sport. During the hottest weeks in July, matches shift to cooler evening times to enhance your comfort. Reservations are recommended for tailgating spaces…
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Wellness & Fitness. Contact: King Family Vineyards. Contact Phone: (434) 823-7800.
Sunday, July 27, 2025, 4:00 PM – 8:00 PM.
For more info visit kingfamilyvineyards.com. Virginia Theatre Festival Presents- Get Happy!
Get Happy! is a dynamic and electric evening celebrating the music and legacy of American icon Judy Garland, performed by acclaimed cabaret artist and UVA alumna Jenna Pastuszek. Rather than imitation, Pastuszek weaves her own story with Garland’s, blending her formidable vocal talents with the allure of timeless standards and hidden gems from the Judy Garland songbook. Audiences will be taken “over the rainbow and then some” in this joyful, heartfelt, and entertaining tribute to one of the world’s greatest entertainers. Perfect for musical lovers and anyone seeking an uplifting night at the theater.
Ticket Details:
Adult tickets: $40–$75 (varies by seat and performance)
Children 12 and under: $5 for all performances.
Event Type: Local Event. Event Category: Art & Culture. Contact: Ruth Caplin Theatre. Contact Phone: (434) 924-3376.
Sunday, July 27, 2025, 5:30 PM – 7:00 PM.
109 Culbreth Rd, Charlottesville, VA 22903.
For more info visit virginiatheatrefestival.org. Farmers in the Park
Charlottesville’s oldest open-air market is back! We offer a little bit of everything. Fresh fruits and veggies, handmade crafts, homemade baked goods, fresh roasted coffee, doughnuts, organic bagels, authentic cultural foods made on location, fresh artisan breads, and much more. You must visit the market; it is truly a taste of Charlottesville.
Event Type: Local Event. Contact: Charlottesville Parks & Recreation. Contact Phone: 434-970-3260.
Wednesday, July 30, 2025, 3:00 PM – 7:00 PM.
Pen Park
1300 Pen Park Road
Charlottesville, VA 22901.
For more info visit www.charlottesville.gov. Fridays After Five
Fridays After Five is Charlottesville’s signature free summer concert series, bringing the community together every Friday evening at Ting Pavilion on the Downtown Mall. Enjoy live performances from a diverse lineup of local and regional bands, spanning genres from rock and pop to soul, bluegrass, and more. Bring your friends and family, grab food and drinks from local vendors, and start your weekend with great music in a lively, family-friendly atmosphere. Rain or shine, it’s the place to be for music lovers and anyone looking for a fun, social Friday night out in the heart of Charlottesville.
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Art & Culture. Entertainment. Contact: Ting Pavilion. Contact Phone: (434) 245-4910.
Friday, August 1, 2025, 5:30 PM – 8:30 PM.
For more info visit www.tingpavilion.com. Charlottesville City Market
Charlottesville’s oldest open-air market is back! We offer a little bit of everything. Fresh fruits and veggies, handmade crafts, homemade baked goods, fresh roasted coffee, doughnuts, organic bagels, authentic cultural foods made on location, fresh artisan breads, and much more. You must visit the market; it is truly a taste of Charlottesville.
Event Type: Local Event. Event Category: Entertainment. Family. Holiday. Wellness & Fitness. Couples. Contact: Charlottesville Parks & Recreation. Contact Phone: 434-970-3260.
Saturday, August 2, 2025, 8:00 AM – 1:00 PM.
100 Water Street
Charlottesville, VA 22902.
For more info visit www.charlottesville.gov. King Family Vineyards (Roseland Polo Club)
Every Sunday from Memorial Day weekend (May 25, 2025) through mid-October (October 12, 2025), weather permitting
Regular match time: 12:00 PM (noon)
Gates open: 10:00 AM
Special summer schedule (July 6 – August 3, 2025): Matches at 5:00 PM and 6:30 PM; gates open at 4:00 PM
Experience the elegance and excitement of polo every Sunday at King Family Vineyards, set against the stunning backdrop of the Blue Ridge Mountains. Watch thrilling polo matches featuring skilled players and their magnificent ponies on the vineyard’s lush fields. Arrive early to enjoy tailgating with family and friends-set up your own space or reserve a spot with or without a tent for shade. Sip award-winning King Family wines, savor food from local vendors, and soak in the festive, welcoming atmosphere. The matches are perfect for all ages, whether you’re a polo enthusiast or new to the sport. During the hottest weeks in July, matches shift to cooler evening times to enhance your comfort. Reservations are recommended for tailgating spaces…
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Wellness & Fitness. Contact: King Family Vineyards. Contact Phone: (434) 823-7800.
Sunday, August 3, 2025, 4:00 PM – 8:00 PM.
For more info visit kingfamilyvineyards.com. Farmers in the Park
Charlottesville’s oldest open-air market is back! We offer a little bit of everything. Fresh fruits and veggies, handmade crafts, homemade baked goods, fresh roasted coffee, doughnuts, organic bagels, authentic cultural foods made on location, fresh artisan breads, and much more. You must visit the market; it is truly a taste of Charlottesville.
Event Type: Local Event. Contact: Charlottesville Parks & Recreation. Contact Phone: 434-970-3260.
Wednesday, August 6, 2025, 3:00 PM – 7:00 PM.
Pen Park
1300 Pen Park Road
Charlottesville, VA 22901.
For more info visit www.charlottesville.gov. Fridays After Five
Fridays After Five is Charlottesville’s signature free summer concert series, bringing the community together every Friday evening at Ting Pavilion on the Downtown Mall. Enjoy live performances from a diverse lineup of local and regional bands, spanning genres from rock and pop to soul, bluegrass, and more. Bring your friends and family, grab food and drinks from local vendors, and start your weekend with great music in a lively, family-friendly atmosphere. Rain or shine, it’s the place to be for music lovers and anyone looking for a fun, social Friday night out in the heart of Charlottesville.
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Art & Culture. Entertainment. Contact: Ting Pavilion. Contact Phone: (434) 245-4910.
Friday, August 8, 2025, 5:30 PM – 8:30 PM.
For more info visit www.tingpavilion.com. Charlottesville City Market
Charlottesville’s oldest open-air market is back! We offer a little bit of everything. Fresh fruits and veggies, handmade crafts, homemade baked goods, fresh roasted coffee, doughnuts, organic bagels, authentic cultural foods made on location, fresh artisan breads, and much more. You must visit the market; it is truly a taste of Charlottesville.
Event Type: Local Event. Event Category: Entertainment. Family. Holiday. Wellness & Fitness. Couples. Contact: Charlottesville Parks & Recreation. Contact Phone: 434-970-3260.
Saturday, August 9, 2025, 8:00 AM – 1:00 PM.
100 Water Street
Charlottesville, VA 22902.
For more info visit www.charlottesville.gov. Rivanna Roots Concert Series
Rivanna Roots is a beloved family-friendly outdoor concert series held on the scenic banks of the Rivanna River. Enjoy an evening of outstanding local and regional music in a relaxed riverside setting. Bring your blanket or chair, savor local craft beer, cider, and wine from exclusive beverage partners, and enjoy delicious offerings from rotating food trucks. Kids 12 and under attend free (please add a free children’s ticket for attendance tracking).
Ticket Prices:
$15 in advance
$18 after 5:00 PM the day before the show and at the door
Kids 12 and under: Free (add free children’s ticket for tracking)
Season Pass: $195 full price (early bird $175 sold out) for all 13 concerts
Tickets support the performing artists and music education programs through The Front Porch Music School. Parking on-site is $5 cash per car; free parking options are available nearby. Dogs on leashes are welcome, and outside food is permitted (no outside alcohol). The event is rain or shine.
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Entertainment. Art & Culture. Couples. Contact: Rivanna River Company. Contact Phone: (434) 218-2052.
Saturday, August 9, 2025, 5:00 PM – 9:00 PM.
For more info visit frontporchcville.org. King Family Vineyards (Roseland Polo Club)
Every Sunday from Memorial Day weekend (May 25, 2025) through mid-October (October 12, 2025), weather permitting
Regular match time: 12:00 PM (noon)
Gates open: 10:00 AM
Special summer schedule (July 6 – August 3, 2025): Matches at 5:00 PM and 6:30 PM; gates open at 4:00 PM
Experience the elegance and excitement of polo every Sunday at King Family Vineyards, set against the stunning backdrop of the Blue Ridge Mountains. Watch thrilling polo matches featuring skilled players and their magnificent ponies on the vineyard’s lush fields. Arrive early to enjoy tailgating with family and friends-set up your own space or reserve a spot with or without a tent for shade. Sip award-winning King Family wines, savor food from local vendors, and soak in the festive, welcoming atmosphere. The matches are perfect for all ages, whether you’re a polo enthusiast or new to the sport. During the hottest weeks in July, matches shift to cooler evening times to enhance your comfort. Reservations are recommended for tailgating spaces…
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Wellness & Fitness. Contact: King Family Vineyards. Contact Phone: (434) 823-7800.
Sunday, August 10, 2025, 10:00 AM – 2:00 PM.
For more info visit kingfamilyvineyards.com. Farmers in the Park
Charlottesville’s oldest open-air market is back! We offer a little bit of everything. Fresh fruits and veggies, handmade crafts, homemade baked goods, fresh roasted coffee, doughnuts, organic bagels, authentic cultural foods made on location, fresh artisan breads, and much more. You must visit the market; it is truly a taste of Charlottesville.
Event Type: Local Event. Contact: Charlottesville Parks & Recreation. Contact Phone: 434-970-3260.
Wednesday, August 13, 2025, 3:00 PM – 7:00 PM.
Pen Park
1300 Pen Park Road
Charlottesville, VA 22901.
For more info visit www.charlottesville.gov. Fridays After Five
Fridays After Five is Charlottesville’s signature free summer concert series, bringing the community together every Friday evening at Ting Pavilion on the Downtown Mall. Enjoy live performances from a diverse lineup of local and regional bands, spanning genres from rock and pop to soul, bluegrass, and more. Bring your friends and family, grab food and drinks from local vendors, and start your weekend with great music in a lively, family-friendly atmosphere. Rain or shine, it’s the place to be for music lovers and anyone looking for a fun, social Friday night out in the heart of Charlottesville.
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Art & Culture. Entertainment. Contact: Ting Pavilion. Contact Phone: (434) 245-4910.
Friday, August 15, 2025, 5:30 PM – 8:30 PM.
For more info visit www.tingpavilion.com. Charlottesville City Market
Charlottesville’s oldest open-air market is back! We offer a little bit of everything. Fresh fruits and veggies, handmade crafts, homemade baked goods, fresh roasted coffee, doughnuts, organic bagels, authentic cultural foods made on location, fresh artisan breads, and much more. You must visit the market; it is truly a taste of Charlottesville.
Event Type: Local Event. Event Category: Entertainment. Family. Holiday. Wellness & Fitness. Couples. Contact: Charlottesville Parks & Recreation. Contact Phone: 434-970-3260.
Saturday, August 16, 2025, 8:00 AM – 1:00 PM.
100 Water Street
Charlottesville, VA 22902.
For more info visit www.charlottesville.gov. King Family Vineyards (Roseland Polo Club)
Every Sunday from Memorial Day weekend (May 25, 2025) through mid-October (October 12, 2025), weather permitting
Regular match time: 12:00 PM (noon)
Gates open: 10:00 AM
Special summer schedule (July 6 – August 3, 2025): Matches at 5:00 PM and 6:30 PM; gates open at 4:00 PM
Experience the elegance and excitement of polo every Sunday at King Family Vineyards, set against the stunning backdrop of the Blue Ridge Mountains. Watch thrilling polo matches featuring skilled players and their magnificent ponies on the vineyard’s lush fields. Arrive early to enjoy tailgating with family and friends-set up your own space or reserve a spot with or without a tent for shade. Sip award-winning King Family wines, savor food from local vendors, and soak in the festive, welcoming atmosphere. The matches are perfect for all ages, whether you’re a polo enthusiast or new to the sport. During the hottest weeks in July, matches shift to cooler evening times to enhance your comfort. Reservations are recommended for tailgating spaces…
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Wellness & Fitness. Contact: King Family Vineyards. Contact Phone: (434) 823-7800.
Sunday, August 17, 2025, 10:00 AM – 2:00 PM.
For more info visit kingfamilyvineyards.com. Farmers in the Park
Charlottesville’s oldest open-air market is back! We offer a little bit of everything. Fresh fruits and veggies, handmade crafts, homemade baked goods, fresh roasted coffee, doughnuts, organic bagels, authentic cultural foods made on location, fresh artisan breads, and much more. You must visit the market; it is truly a taste of Charlottesville.
Event Type: Local Event. Contact: Charlottesville Parks & Recreation. Contact Phone: 434-970-3260.
Wednesday, August 20, 2025, 3:00 PM – 7:00 PM.
Pen Park
1300 Pen Park Road
Charlottesville, VA 22901.
For more info visit www.charlottesville.gov. Scottsville’s Summer Concert Series
Fridays on the Canal is Scottsville’s new favorite way to kick off the weekend! Held on the fourth Friday of each month from May through September, this free summer concert series brings our riverside community together with live music, food trucks, wine & beer, and local vendors.
🎸 Free Admission
🍔 Family-Friendly
🕔 5–8 PM | Fourth Fridays | May–September.
Property: Omni Charlottesville Hotel. Event Type: Local Event.
Friday, August 22, 2025, 5:00 PM – 8:00 PM.
For more info visit fridaysonthecanal.com. Fridays After Five
Fridays After Five is Charlottesville’s signature free summer concert series, bringing the community together every Friday evening at Ting Pavilion on the Downtown Mall. Enjoy live performances from a diverse lineup of local and regional bands, spanning genres from rock and pop to soul, bluegrass, and more. Bring your friends and family, grab food and drinks from local vendors, and start your weekend with great music in a lively, family-friendly atmosphere. Rain or shine, it’s the place to be for music lovers and anyone looking for a fun, social Friday night out in the heart of Charlottesville.
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Art & Culture. Entertainment. Contact: Ting Pavilion. Contact Phone: (434) 245-4910.
Friday, August 22, 2025, 5:30 PM – 8:30 PM.
For more info visit www.tingpavilion.com. Charlottesville City Market
Charlottesville’s oldest open-air market is back! We offer a little bit of everything. Fresh fruits and veggies, handmade crafts, homemade baked goods, fresh roasted coffee, doughnuts, organic bagels, authentic cultural foods made on location, fresh artisan breads, and much more. You must visit the market; it is truly a taste of Charlottesville.
Event Type: Local Event. Event Category: Entertainment. Family. Holiday. Wellness & Fitness. Couples. Contact: Charlottesville Parks & Recreation. Contact Phone: 434-970-3260.
Saturday, August 23, 2025, 8:00 AM – 1:00 PM.
100 Water Street
Charlottesville, VA 22902.
For more info visit www.charlottesville.gov. Rivanna Roots Concert Series
Rivanna Roots is a beloved family-friendly outdoor concert series held on the scenic banks of the Rivanna River. Enjoy an evening of outstanding local and regional music in a relaxed riverside setting. Bring your blanket or chair, savor local craft beer, cider, and wine from exclusive beverage partners, and enjoy delicious offerings from rotating food trucks. Kids 12 and under attend free (please add a free children’s ticket for attendance tracking).
Ticket Prices:
$15 in advance
$18 after 5:00 PM the day before the show and at the door
Kids 12 and under: Free (add free children’s ticket for tracking)
Season Pass: $195 full price (early bird $175 sold out) for all 13 concerts
Tickets support the performing artists and music education programs through The Front Porch Music School. Parking on-site is $5 cash per car; free parking options are available nearby. Dogs on leashes are welcome, and outside food is permitted (no outside alcohol). The event is rain or shine.
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Entertainment. Art & Culture. Couples. Contact: Rivanna River Company. Contact Phone: (434) 218-2052.
Saturday, August 23, 2025, 5:00 PM – 9:00 PM.
For more info visit frontporchcville.org. King Family Vineyards (Roseland Polo Club)
Every Sunday from Memorial Day weekend (May 25, 2025) through mid-October (October 12, 2025), weather permitting
Regular match time: 12:00 PM (noon)
Gates open: 10:00 AM
Special summer schedule (July 6 – August 3, 2025): Matches at 5:00 PM and 6:30 PM; gates open at 4:00 PM
Experience the elegance and excitement of polo every Sunday at King Family Vineyards, set against the stunning backdrop of the Blue Ridge Mountains. Watch thrilling polo matches featuring skilled players and their magnificent ponies on the vineyard’s lush fields. Arrive early to enjoy tailgating with family and friends-set up your own space or reserve a spot with or without a tent for shade. Sip award-winning King Family wines, savor food from local vendors, and soak in the festive, welcoming atmosphere. The matches are perfect for all ages, whether you’re a polo enthusiast or new to the sport. During the hottest weeks in July, matches shift to cooler evening times to enhance your comfort. Reservations are recommended for tailgating spaces…
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Wellness & Fitness. Contact: King Family Vineyards. Contact Phone: (434) 823-7800.
Sunday, August 24, 2025, 10:00 AM – 2:00 PM.
For more info visit kingfamilyvineyards.com. Farmers in the Park
Charlottesville’s oldest open-air market is back! We offer a little bit of everything. Fresh fruits and veggies, handmade crafts, homemade baked goods, fresh roasted coffee, doughnuts, organic bagels, authentic cultural foods made on location, fresh artisan breads, and much more. You must visit the market; it is truly a taste of Charlottesville.
Event Type: Local Event. Contact: Charlottesville Parks & Recreation. Contact Phone: 434-970-3260.
Wednesday, August 27, 2025, 3:00 PM – 7:00 PM.
Pen Park
1300 Pen Park Road
Charlottesville, VA 22901.
For more info visit www.charlottesville.gov. Fridays After Five
Fridays After Five is Charlottesville’s signature free summer concert series, bringing the community together every Friday evening at Ting Pavilion on the Downtown Mall. Enjoy live performances from a diverse lineup of local and regional bands, spanning genres from rock and pop to soul, bluegrass, and more. Bring your friends and family, grab food and drinks from local vendors, and start your weekend with great music in a lively, family-friendly atmosphere. Rain or shine, it’s the place to be for music lovers and anyone looking for a fun, social Friday night out in the heart of Charlottesville.
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Art & Culture. Entertainment. Contact: Ting Pavilion. Contact Phone: (434) 245-4910.
Friday, August 29, 2025, 5:30 PM – 8:30 PM.
For more info visit www.tingpavilion.com. Charlottesville City Market
Charlottesville’s oldest open-air market is back! We offer a little bit of everything. Fresh fruits and veggies, handmade crafts, homemade baked goods, fresh roasted coffee, doughnuts, organic bagels, authentic cultural foods made on location, fresh artisan breads, and much more. You must visit the market; it is truly a taste of Charlottesville.
Event Type: Local Event. Event Category: Entertainment. Family. Holiday. Wellness & Fitness. Couples. Contact: Charlottesville Parks & Recreation. Contact Phone: 434-970-3260.
Saturday, August 30, 2025, 8:00 AM – 1:00 PM.
100 Water Street
Charlottesville, VA 22902.
For more info visit www.charlottesville.gov. King Family Vineyards (Roseland Polo Club)
Every Sunday from Memorial Day weekend (May 25, 2025) through mid-October (October 12, 2025), weather permitting
Regular match time: 12:00 PM (noon)
Gates open: 10:00 AM
Special summer schedule (July 6 – August 3, 2025): Matches at 5:00 PM and 6:30 PM; gates open at 4:00 PM
Experience the elegance and excitement of polo every Sunday at King Family Vineyards, set against the stunning backdrop of the Blue Ridge Mountains. Watch thrilling polo matches featuring skilled players and their magnificent ponies on the vineyard’s lush fields. Arrive early to enjoy tailgating with family and friends-set up your own space or reserve a spot with or without a tent for shade. Sip award-winning King Family wines, savor food from local vendors, and soak in the festive, welcoming atmosphere. The matches are perfect for all ages, whether you’re a polo enthusiast or new to the sport. During the hottest weeks in July, matches shift to cooler evening times to enhance your comfort. Reservations are recommended for tailgating spaces…
Property: Omni Charlottesville Hotel. Event Type: Local Event. Event Category: Wellness & Fitness. Contact: King Family Vineyards. Contact Phone: (434) 823-7800.
Sunday, August 31, 2025, 10:00 AM – 2:00 PM.
For more info visit kingfamilyvineyards.com. Farmers in the Park
Charlottesville’s oldest open-air market is back! We offer a little bit of everything. Fresh fruits and veggies, handmade crafts, homemade baked goods, fresh roasted coffee, doughnuts, organic bagels, authentic cultural foods made on location, fresh artisan breads, and much more. You must visit the market; it is truly a taste of Charlottesville.
Event Type: Local Event. Contact: Charlottesville Parks & Recreation. Contact Phone: 434-970-3260.
Wednesday, September 3, 2025, 3:00 PM – 7:00 PM.
Pen Park
1300 Pen Park Road
Charlottesville, VA 22901.
For more info visit www.charlottesville.gov.