Parenting Pressures: Navigating Challenges and Achieving Balance
Event Details
Parents are under more pressure than ever, with increasing work demands, societal expectations, concerns about children’s safety and the influence of social media, and often the added burden of caring for their own parents. This event, presented in conjunction with Positive Directions, will explore these current realities, sharing ways for parents to stay present and take care of themselves.
The event will feature a panel of local mental health experts, followed by small-group discussions that will allow participants to ask questions, share resources, and receive guided support.
Why You Should Come
Because being a parent is hard, we can all use some help and a few tips to help us achieve a better balance. The purpose of this panel is to address current parental realities. Panel members represent a number of different stakeholders, allowing for a multifaceted exploration of a range of topics, including: parenting youth in Westport’s achievement culture; balancing work life and parenting; balanc…
Category: Children and Families. Education. Lectures, Presentations, Workshops.
Monday, September 15, 2025, 7:00 PM – 8:00 PM.
Westport Library
20 Jesup Road
Westport, CT 06880.
For more info visit westportlibrary.org. CLUB203 - BARNYARD BASH!
Join CLUB203 for a fun-filled evening at Lachat Town Farm for a Barnyard Bash!
Come dressed in your favorite flannel shirts and cowboy hats, and get ready to kick up your heels with lively line dancing.
Enjoy games, treats, and art by MoCA.
The Barnyard Bash promises an unforgettable night of community fun and farm charm!
Category: Community.
Tuesday, September 16, 2025, 6:30 PM – 8:00 PM.
Lachat Town Farm
106 Godfrey Road West
Weston, CT 06883.
For more info visit club203.org. Sip & Celebrate Climate Action w/ Rep. Steinberg
Start your day with a cup of coffee and meaningful conversation! Join CTLCV and Representative Jonathan Steinberg at the Westport Library as we reflect on the climate wins from the 2025 legislative session and look ahead to the work still to come. This is a great opportunity to connect with fellow climate advocates, share ideas, and get inspired to take action for a healthier, greener Connecticut.
Category: Environmental Meetings.
Wednesday, September 17, 2025, 9:30 AM – 10:30 AM.
Westport Library, Board Room, 20 Jesup Rd, Westport, CT 06880.
For more info visit secure.everyaction.com. Free Stop the Bleed Class
STOP THE BLEED® Certification Class:
The American College of Surgeons’ STOP THE BLEED® program turns ordinary bystanders into immediate responders, giving you the skills to control life‑threatening bleeding before professional help arrives - at home, at work, or on the road.
In just 90 minutes you’ll learn—and practice—the three proven techniques that save lives:
Apply focused pressure to the wound
Pack and compress deep injuries
Apply a tourniquet correctly and safely.
Category: Education.
Wednesday, September 17, 2025, 7:00 PM – 8:30 PM.
Westport Volunteer EMS Headquarters: 50 Jesup Road, Westport, CT.
For more info visit www.westportems.org. Westport Farmers Market
Under the leadership of our Executive Director, Lori Cochran-Dougall, the Westport Farmers’ Market is recognized in Connecticut for its leadership in implementing the highest vendor standards and guidelines in the state, curating meaningful community outreach and programming and elevating environmental standards within this farmers' market and beyond. The market’s entrenchment in the community of outstanding chefs coupled with engaged corporate and community sponsors makes the Westport Farmers’ Market the central hub of the food community in Fairfield County and beyond. With 50+ highly curated vendors, we welcome thousands of shoppers into our community every week.
Come see what all of the talk is about!
Category: Community. Fair/Festival. Music. Outdoors/Recreation. Seasonal.
Thursday, September 18, 2025, 10:00 AM – 2:00 PM.
50 Imperial Avenue, Westport.
For more info visit www.westportfarmersmarket.com. Sound Bath with Abbey Chase Yoga at Earthplace
Discover the rest, recovery, and healing that sound can bring! A Sound Bath is a meditative and therapeutic experience that uses the vibrations produced by sound to promote deep relaxation and healing. These vibrations resonate within the body’s cells, promoting profound emotional, mental, spiritual, and even physical benefits. You will leave feeling relaxed, peaceful, light, and clear.
Sound Bath sessions will be held outdoors on the serene and beautiful grounds of our nature center, weather permitting. Bring your own yoga mat, blanket, or outdoor chair. In the case of inclement weather, sessions will move indoors.
Pre-registration is required. Limited spaces available, register today!
Category: Outdoors/Recreation. Community.
Thursday, September 18, 2025, 6:00 PM – 7:15 PM.
Earthplace
10 Woodside Lane
Westport, CT.
For more info visit earthplace.app.neoncrm.com. "Dooley at the Bar"
"Dooley at the Bar" brings Gilded Age wit to Westport Community Theatre as Chicago’s legendary bartender-philosopher, created by Finley Peter Dunne, comes to life in a one-man performance by Alexander Kulcsar. Directed by Michael Stanley, the play opens WCT’s 68th Season, running September 12–28, 2025.
Category: Theater.
Thursday, September 18, 2025, 7:30 PM – 8:50 PM.
Westport Community Theatre.
For more info visit westportcommunitytheatre.com. "Dooley at the Bar"
"Dooley at the Bar" brings Gilded Age wit to Westport Community Theatre as Chicago’s legendary bartender-philosopher, created by Finley Peter Dunne, comes to life in a one-man performance by Alexander Kulcsar. Directed by Michael Stanley, the play opens WCT’s 68th Season, running September 12–28, 2025.
Category: Theater.
Friday, September 19, 2025, 7:30 PM – 8:50 PM.
Westport Community Theatre.
For more info visit westportcommunitytheatre.com. APDA Optimism Walk
Please join us for the American Parkinson Disease Association, CT Chapter, Optimism Walk in Westport on September 20.
Category: Community.
Saturday, September 20, 2025, 10:00 AM – 2:00 PM.
Sherwood Island.
For more info visit secure.qgiv.com. PopShop Market Returns to Westport – Saturday, September 20th
PopShop Market is back on Saturday, September 20th from 10:00 AM – 3:00 PM on the beautiful grounds of the Westport Museum for History and Culture. This highly anticipated community event brings together a juried selection of elevated vendors, offering a thoughtfully curated shopping experience for all ages.
Visitors will discover:
* Handcrafted Jewelry ✨
* Curated Vintage & Antique Finds 🕰️
* Clothing for Adults & Children 👗👕
* Unique Gifts & Lifestyle Goods 🎁
Supporting small, local makers and shops, PopShop Market celebrates creativity, craftsmanship, and community. Shoppers are encouraged to come spend the day, explore downtown Westport, and enjoy this festive open-air market.
Event Details:
📍 Location: Westport Museum for History and Culture
🗓️ Date: Saturday, September 20, 2025
⏰ Time: 10:00 AM – 3:00 PM
🎟️ Admission: Free & Open to the Public
🐾 Dog-Friendly Event
🅿️ Plenty of parking available at City Hall and throughout down…
Category: Fair/Festival.
Saturday, September 20, 2025, 10:00 AM – 3:00 PM.
Westport Museum For History and Culture
25 Avery Place
Westport, CT 06880.
For more info visit www.popshopmarketct.com. Westport Rotary Annual LobsterFest 2025
14th Annual Westport Rotary LobsterFest to raise funds for local, regional and international humanitarian causes. Great Family Event with band, activities for kids, includes beer, wine and other beverages.
Price includes either 2 lobsters or a 13 oz steak. Kids meals for age 3-12. Note: date for the event is correct, subject to getting the final town permits.
Category: Fair/Festival. Fundraising Events.
Saturday, September 20, 2025, 3:00 PM – 7:00 PM.
Compo Beach.
Endless Summer at MoCA \ CT
Join the Museum of Contemporary Art \ CT for Endless Summer, an unforgettable evening of music, art, conversation, and refreshments in support of MoCA \ CT’s mission.
What makes the night special:
* An intimate look at Tod Papageorge's evocative At the Beach exhibition
* Culinary artistry with delicious coastal-inspired bites
* Handcrafted cocktails MoCA-tails designed to complement the atmosphere
* Live music from the celebrated Arthur Lipner Trio
* Artisanal gelato from Pierluigi Mazzella’s acclaimed Fatto a Mano bakery in Westport
* Genuine connections and community with people who believe art can change the world
Tickets are available at https://givebutter.com/endlesssummer
Museum of Contemporary Art \ CT
19 Newtown Turnpike, Westport, CT.
mocact.org.
Category: Fundraising Events.
Saturday, September 20, 2025, 6:00 PM – 9:00 PM.
Museum of Contemporary Art \ CT
19 Newtown Turnpike
Westport, CT 06880.
For more info visit mocact.org. ARGONAUT & WASP W/S/G WILD & CO: Free Concert
FREE TICKET SHOW | SATURDAY, SEPT 20 | 7.00PM / DOORS 6:00PM
A full bar and food truck(s) will be open and on site for this show.
Outside food and drink is allowed at this free event.
Note: If you reserved a free ticket for 7/31, you are all set; your bar-coded ticket will work on 9/20.
Argonaut & Wasp is the Brooklyn based band known for their infectious grooves, catchy vocals, and explosive live performances. Formed by a chance meeting in a dorm room, they have grown to become a NYC mainstay, selling out residencies and rooms like Elsewhere, Rough Trade, Music Hall of Williamsburg, Bowery Ballroom, etc. “All across the country, dancers are boogieing to the clang of guitars and singing along to original vocal hooks like it’s Manchester circa 1983, but in NYC, it’s Argonaut & Wasp supplying the infectious hooks.” – BILLBOARD.
Their debut album “STARLIGHT 99” was released in 2021 after spending much of 2020 quarantine writing & producing. Featuring tracks like “Monacillo” “Composure” feat…
Category: Music. Outdoors/Recreation.
Saturday, September 20, 2025, 7:00 PM – 8:30 PM.
40 Jesup Rd, Westport, CT 06880.
For more info visit ci.ovationtix.com. "Dooley at the Bar"
"Dooley at the Bar" brings Gilded Age wit to Westport Community Theatre as Chicago’s legendary bartender-philosopher, created by Finley Peter Dunne, comes to life in a one-man performance by Alexander Kulcsar. Directed by Michael Stanley, the play opens WCT’s 68th Season, running September 12–28, 2025.
Category: Theater.
Saturday, September 20, 2025, 7:30 PM – 8:50 PM.
Westport Community Theatre.
For more info visit westportcommunitytheatre.com. "Dooley at the Bar"
"Dooley at the Bar" brings Gilded Age wit to Westport Community Theatre as Chicago’s legendary bartender-philosopher, created by Finley Peter Dunne, comes to life in a one-man performance by Alexander Kulcsar. Directed by Michael Stanley, the play opens WCT’s 68th Season, running September 12–28, 2025.
Category: Theater.
Sunday, September 21, 2025, 2:00 PM – 3:20 PM.
Westport Community Theatre.
For more info visit westportcommunitytheatre.com. Chamber Music w/ Harp at Weston Library September 21
Canta Libre Brings Harp, Flute and Strings to Sep. 21 Concert in Weston
The Friends of the Weston Library announce the beginning of their third season of Sunday Soundscapes concerts, beginning September 21 with the chamber ensemble Canta Libre.
Canta Libre was founded in 2002 by flutist Sally Shorrock to foster the performance and enjoyment of musical literature specifically written for flute, harp and strings. They have been acclaimed by audiences throughout the Northeast.
They were featured at The American Harp Society 50th Anniversary National Conference, and have appeared at Lincoln Center, on WNYC at The Green Space, The Music Festival of the Hamptons, Barge Music, Concerts at One at Trinity Church in Manhattan, WLIW TV, National Public Radio of Long Island, and The Brooklyn Public Library. Trained at the finest conservatories, many of the members have performed and toured internationally with appearances at major festivals, including Aspen, Spoleto and Tanglewood.
Their critically-acclaimed CD of music…
Category: Classical Music.
Sunday, September 21, 2025, 4:00 PM – 6:00 PM.
Weston Public Library.
For more info visit www.eventbrite.com. Westport Farmers Market
Under the leadership of our Executive Director, Lori Cochran-Dougall, the Westport Farmers’ Market is recognized in Connecticut for its leadership in implementing the highest vendor standards and guidelines in the state, curating meaningful community outreach and programming and elevating environmental standards within this farmers' market and beyond. The market’s entrenchment in the community of outstanding chefs coupled with engaged corporate and community sponsors makes the Westport Farmers’ Market the central hub of the food community in Fairfield County and beyond. With 50+ highly curated vendors, we welcome thousands of shoppers into our community every week.
Come see what all of the talk is about!
Category: Community. Fair/Festival. Music. Outdoors/Recreation. Seasonal.
Thursday, September 25, 2025, 10:00 AM – 2:00 PM.
50 Imperial Avenue, Westport.
For more info visit www.westportfarmersmarket.com. Free QPR Suicide Prevention Training
Question-Persuade-Refer (QPR) is an evidence-based training for the general public (ages 16+). We encourage everyone to receive the training! Learn how to reach out to someone who may be struggling and provide life-saving support. The training includes videos, a slideshow, and a group role play.
For 2025, we are offering this training for free bimonthly on last Fridays from 12-1:30pm. Please note that at least 5 attendees are required for a training to take place. We also ask you not to attend any suicide prevention training if you have been personally affected by suicide in the past 6 months.
We offer QPR group trainings to organizations in our catchment area upon request (English or Spanish), as well as other training programs. Please email Margaret at mwatt@positivedirections.org if interested in this option.
RSVP via the web link!
Category: Education. Lectures, Presentations, Workshops.
Friday, September 26, 2025, 12:00 PM – 1:30 PM.
Positive Directions, 90 Post Rd W, Westport, CT 06880.
For more info visit www.positivedirections.org. "Dooley at the Bar"
"Dooley at the Bar" brings Gilded Age wit to Westport Community Theatre as Chicago’s legendary bartender-philosopher, created by Finley Peter Dunne, comes to life in a one-man performance by Alexander Kulcsar. Directed by Michael Stanley, the play opens WCT’s 68th Season, running September 12–28, 2025.
Category: Theater.
Friday, September 26, 2025, 7:30 PM – 8:50 PM.
Westport Community Theatre.
For more info visit westportcommunitytheatre.com. Destination Westport: Black Stories
Explore Westport’s Hidden African American History – Special Tours on Juneteenth & Beyond!
Step back in time and discover the powerful, untold stories of Westport’s African American community! Join us for a guided walking tour through downtown Westport, based on the Museum’s award-winning exhibit Remembered: The History of African Americans in Westport.
Commemorate Juneteenth with a journey through history, from the days of enslavement to the present, and learn how African Americans shaped Westport’s identity. Not able to make it on Juneteenth? Don’t worry — we’ve got another tour later on, too!
Westport Museum’s Staff will share the stories of soldiers, sailors, activists, artists, and respected citizens whose legacies are woven into the fabric of this town. Visit historic sites and buildings, some still standing, others long gone. Explore this rich history firsthand and follow along with our Remembered virtual exhibit available online.
The tour will meet at the Westport Museum’s brick walk along Myr…
Category: History.
Saturday, September 27, 2025, 9:30 AM – 11:00 AM.
Westport Museum for History and Culture.
For more info visit westporthistory.org. The Fitzgeralds: A Reading with Music
Alec Baldwin and Stephanie Zimbalist star in
"The Fitzgeralds: A Reading with Music," marking the centennial of "The Great Gatsby," one of the most enduring works of American literature.
At the heart of this performance lies the extraordinary correspondence between F. Scott and Zelda Fitzgerald — letters that reveal a relationship shaped by ambition, artistry, and emotional complexity. Through their own words, we encounter two singular voices whose love and conflict fueled some of the most iconic writing of the 20th century.
Category: Theater.
Saturday, September 27, 2025, 7:00 PM – 8:30 PM.
Westport Country Playhouse.
For more info visit www.westportplayhouse.org. "Dooley at the Bar"
"Dooley at the Bar" brings Gilded Age wit to Westport Community Theatre as Chicago’s legendary bartender-philosopher, created by Finley Peter Dunne, comes to life in a one-man performance by Alexander Kulcsar. Directed by Michael Stanley, the play opens WCT’s 68th Season, running September 12–28, 2025.
Category: Theater.
Saturday, September 27, 2025, 7:30 PM – 8:50 PM.
Westport Community Theatre.
For more info visit westportcommunitytheatre.com. Bigelow Tea BTCC
Whether you're racing for a personal best or enjoying a leisurely walk with family and friends, the Bigelow Tea Community Challenge is a great way to give back to our community while having fun!
Registration Includes:
✔️ The 38th Annual BTCC T-shirt
✔️ A heavy goodie bag filled with treats and gifts from local and sustainable partners
✔️ A raffle ticket for a chance to win exciting prizes after the race! (Must be present to win)
Kids' Fun Run
(For kids 10 and under) Includes a 100-yard scamper, 1-mile jog, or obstacle course held on the turf field at Wakeman's Club
These activities are not timed.
Category: Children and Families. Community. Outdoors/Recreation. Sports.
Sunday, September 28, 2025, 8:00 AM – 1:00 PM.
Wakemans Boys and Girls Club - Southport.
For more info visit runsignup.com. Woodland Harvest: Foraging in Fall
Learn to safely and sustainably enjoy goods from the woods available in autumn. Join Earthplace naturalist Siobhan Prout on a short walk outside and learn how to gather and prepare the edible foods growing in our sanctuary and garden.
Category: Children and Families. Community. Education. Environmental Meetings. Hobbies. Lectures, Presentations, Workshops. Outdoors/Recreation. Seasonal.
Sunday, September 28, 2025, 1:00 PM – 2:30 PM.
Earthplace
10 Woodside Lane
Westport, CT.
For more info visit earthplace.app.neoncrm.com. "Dooley at the Bar"
"Dooley at the Bar" brings Gilded Age wit to Westport Community Theatre as Chicago’s legendary bartender-philosopher, created by Finley Peter Dunne, comes to life in a one-man performance by Alexander Kulcsar. Directed by Michael Stanley, the play opens WCT’s 68th Season, running September 12–28, 2025.
Category: Theater.
Sunday, September 28, 2025, 2:00 PM – 3:20 PM.
Westport Community Theatre.
For more info visit westportcommunitytheatre.com. Westport Farmers Market
Under the leadership of our Executive Director, Lori Cochran-Dougall, the Westport Farmers’ Market is recognized in Connecticut for its leadership in implementing the highest vendor standards and guidelines in the state, curating meaningful community outreach and programming and elevating environmental standards within this farmers' market and beyond. The market’s entrenchment in the community of outstanding chefs coupled with engaged corporate and community sponsors makes the Westport Farmers’ Market the central hub of the food community in Fairfield County and beyond. With 50+ highly curated vendors, we welcome thousands of shoppers into our community every week.
Come see what all of the talk is about!
Category: Community. Fair/Festival. Music. Outdoors/Recreation. Seasonal.
Thursday, October 2, 2025, 10:00 AM – 2:00 PM.
50 Imperial Avenue, Westport.
For more info visit www.westportfarmersmarket.com. Free First Saturdays
First Saturdays are a great opportunity to experience what we have to offer at the Westport Museum free of charge on the first Saturday of each month.
Young visitors can enjoy a scavenger hunt in the museum, the diorama of Westport featuring an audio tour by Joanne Woodward, coloring pages, colonial games and more. Adult visitors will enjoy our wide array of exhibits. Our 2025 exhibition, Playful Pastimes 1890-1910, is on view as well as our local history gallery
More info below:
https://westporthistory.org/event/free-first-saturdays-2/2025-01-04/
Westport Museum is accessible via public transit! The Westport-Saugatuck railroad station has connections on the MTA New Haven line from Norwalk, Bridgeport, Stratford, Milford, and New Haven, and more. Uber 2.3 miles to the Museum or take the Norwalk Wheels bus transit system when available to Post Road West at Myrtle Avenue, which is a brief 7-minute walk from the Museum!
Park on Myrtle Avenue and Avery Place or behind Westport Town Hall or…
Category: Children and Families.
Saturday, October 4, 2025, 11:00 AM – 5:00 PM.
Westport Museum.
Westoberfest Craft Beer & Family Fall Festival
Dust off your lederhosen and dirndls! Westoberfest returns Saturday, October 4, in downtown Westport!
Celebrate fall at the 8th Annual Craft Beer & Family Fall Festival, a vibrant downtown celebration featuring local craft breweries, live music, family-friendly activities, food trucks, market vendors, competitions, and more.
Festival Admission: Includes access to all festival activities, including live music, kids' activities, food, vendors, competitions, and more.
Beer Tasting Tent (21+): Grab your 2025 commemorative glass and enjoy unlimited tastings from local and regional breweries from 1 to 5 p.m.
Tickets on sale now at westportdowntown.com/westoberfest.
Buy early and save as prices increase at the door!
Category: Children and Families. Community. Fair/Festival. Music. Outdoors/Recreation. Seasonal.
Saturday, October 4, 2025, 12:00 PM – 6:00 PM.
Downtown Westport | Sigrid Schultz Plaza - Elm St.
For more info visit westportdowntown.com. Panel Discussion with Tod Papageorge + Yale MFA alums
MoCA CT presents a panel discussion between exhibiting artist, Tod Papageorge and a select few alumni such as John Pilson from the Yale School of Art to discuss the history, present and future of education on photography. This conversation will be moderated by the exhibition organizer, photographer and educator, Lisa Kereszi.
Category: Art Exhibition.
Saturday, October 4, 2025, 4:00 PM – 5:00 PM.
19 Newtown Turnpike Westport, CT 06880.
For more info visit mocact.org. Fundraising Gala - At This Stage
A gala evening celebrating Westport Country Playhouse’s 95 Seasons!
Join us on October 4th as we celebrate Artistic Honoree NATHAN LANE and Playhouse Leadership Award Winner ANNE KEEFE!
Category: Fundraising Events.
Saturday, October 4, 2025, 7:00 PM – 9:00 PM.
Westport Country Playhouse.
For more info visit www.westportplayhouse.org. Woodside Bash
Fundraiser event at Earthplace! Enjoy an open bar, harvest dinner, live entertainment, a roaring fire pit, and the mechanical bull! (21+).
Category: Community. Environmental Meetings. Fair/Festival. Fundraising Events. Music. Outdoors/Recreation. Seasonal.
Saturday, October 4, 2025, 7:00 PM – 10:00 PM.
Earthplace
10 Woodside Lane
Westport, CT 06880.
For more info visit earthplace.org. Caravan of Thieves
On Saturday evening, October 4th at 8:00pm the zany group that is Caravan of Thieves returns to bring their magic to Voices Cafe.
Caravan of Thieves is renowned for their mesmerizing vocal harmonies, pure entertainment, and dazzling performances.
For tickets go to: voicescafe.org.
This concert is on Saturday, October 4th. Doors open at 7:30pm, with showtime at 8:00pm. Tickets and information are available at voicescafe.org. General admission is $28 per ticket.
Voices Cafe offers a BYO setting with a choice of coffee-house style seating at tables or individual seating, and guests are welcome to bring their own beverages and snacks. Groups of four or more can reserve table space.
Voices Cafe concerts support social justice programs in our local community. Concerts are held at The Unitarian Universalist Congregation in Westport, located at 10 Lyons Plains Road in Westport.
Category: Music.
Saturday, October 4, 2025, 8:00 PM – 10:30 PM.
Voices Cafe
10 Lyons Plains Road, Westport CT 06880.
For more info visit voicescafe.org. Fall Festival
Fundraiser event at Earthplace! A family fun day featuring food trucks, a corn pool, apple slingshot, donut on a string, nature exploration, animal encounters, and more!
Category: Children and Families. Community. Environmental Meetings. Fair/Festival. Fundraising Events. Music. Outdoors/Recreation. Seasonal.
Sunday, October 5, 2025, 10:00 AM – 3:00 PM.
Earthplace
10 Woodside Lane
Westport, CT 06880.
For more info visit earthplace.org. Winged Wonders
First Sunday of the month, 1pm. Experience our birds of prey outside their enclosures! On the first Sunday of the month we host a bird-on-glove demonstration where you can learn all about some of our magnificent raptors. Naturalists will discuss the animals' traits, behaviors, and unique characteristics while the birds interact with their handlers.
FREE with admission to Earthplace!
Category: Children and Families. Education. Lectures, Presentations, Workshops.
Sunday, October 5, 2025, 1:00 PM.
Earthplace, 10 Woodside Lane, Westport, CT 06880.
For more info visit earthplace.org. Destination Westport: Westport Sanitarium
This Halloween season, dare to uncover the chilling past of Westport’s lost sanitariums, where heartbreak, psychological control, and eerie medical practices once thrived. Though the buildings have vanished, the spirits remain—haunting the grounds of Winslow Park.
Join us for a spine-tingling tour through this historic site, where you’ll hear real stories of the doctors, administrators, and patients who once walked these halls. As you explore, you’ll see haunting images and uncover secrets that linger in the shadows—tales of life, death, and the unexplained.
From the unsettling reality of early mental health treatments to the restless souls who may still roam, this is your chance to experience the darker side of Westport’s history. Are you brave enough to step into the past?
Meet us at the cement path in front of the parking lot along Compo Road North. We recommend wearing comfortable walking shoes and bringing bottled water, as the ground is uneven and the weather may be warm. Be prepared for a chillin…
Category: History.
Thursday, October 9, 2025, 10:00 AM – 11:00 AM.
Winslow Park.
For more info visit westporthistory.org. Westport Farmers Market
Under the leadership of our Executive Director, Lori Cochran-Dougall, the Westport Farmers’ Market is recognized in Connecticut for its leadership in implementing the highest vendor standards and guidelines in the state, curating meaningful community outreach and programming and elevating environmental standards within this farmers' market and beyond. The market’s entrenchment in the community of outstanding chefs coupled with engaged corporate and community sponsors makes the Westport Farmers’ Market the central hub of the food community in Fairfield County and beyond. With 50+ highly curated vendors, we welcome thousands of shoppers into our community every week.
Come see what all of the talk is about!
Category: Community. Fair/Festival. Music. Outdoors/Recreation. Seasonal.
Thursday, October 9, 2025, 10:00 AM – 2:00 PM.
50 Imperial Avenue, Westport.
For more info visit www.westportfarmersmarket.com. Colin Quinn
From MTV’s “Remote Control” to “Saturday Night Live“ to Comedy Central’s “Tough Crowd with Colin Quinn”.
Category: Theater.
Thursday, October 9, 2025, 8:00 PM – 10:00 PM.
Westport Country Playhouse.
For more info visit www.westportplayhouse.org. Psycho
Psycho (1960), directed by Alfred Hitchcock, is a landmark psychological horror film that redefined the genre. The story follows Marion Crane (Janet Leigh), who embezzles money and seeks refuge at the secluded Bates Motel, run by the enigmatic Norman Bates (Anthony Perkins). What begins as a suspenseful encounter soon spirals into a chilling tale of deception and madness, culminating in one of the most iconic scenes in cinematic history. Post-show talk by Mark Shanahan, Westport Country Playhouse Artistic Director.
Category: Movies/Film.
Friday, October 10, 2025, 7:00 PM – 9:00 PM.
Westport Country Playhouse.
For more info visit www.westportplayhouse.org. Westport Farmers Market
Under the leadership of our Executive Director, Lori Cochran-Dougall, the Westport Farmers’ Market is recognized in Connecticut for its leadership in implementing the highest vendor standards and guidelines in the state, curating meaningful community outreach and programming and elevating environmental standards within this farmers' market and beyond. The market’s entrenchment in the community of outstanding chefs coupled with engaged corporate and community sponsors makes the Westport Farmers’ Market the central hub of the food community in Fairfield County and beyond. With 50+ highly curated vendors, we welcome thousands of shoppers into our community every week.
Come see what all of the talk is about!
Category: Community. Fair/Festival. Music. Outdoors/Recreation. Seasonal.
Thursday, October 16, 2025, 10:00 AM – 2:00 PM.
50 Imperial Avenue, Westport.
For more info visit www.westportfarmersmarket.com. Stand Up for Homes with Hope
We are thrilled to return to the Quick Center this fall for another Stand Up for Homes with Hope! Our featured comedian, Tom Papa, has more than 20 years as a stand-up comedian, and is one of the top comedic voices in the country, finding success as an actor, host, and author, in film, TV, radio and podcasts as well as on the live stage.
Category: Community. Theater.
Friday, October 17, 2025, 7:00 PM – 9:00 PM.
Quick Center for the Arts, Fairfield University, Fairfield.
Mushroom Growing Workshop
Join us for this hands-on mushroom growing and log inoculation workshop led by Earthplace naturalist Siobhan Prout. Experience the magic and mystery of hyphae as you learn to cultivate mushrooms and take home your own inoculated log.
One ticket = 1 log. Registration closes one week before the workshop.
Participants must be at least 12 years old.
Category: Education. Community. Seasonal. Outdoors/Recreation. Lectures, Presentations, Workshops. Hobbies. Environmental Meetings. Children and Families.
Sunday, October 19, 2025, 1:00 PM – 3:00 PM.
Earthplace
10 Woodside Lane
Westport, CT.
For more info visit earthplace.app.neoncrm.com. Performing Arts at MoCA: Caity Gyorgy (Jazz)
Discover the thrill of live jazz at MoCA\CT with Caity Gyorgy, a three-time JUNO Award-winning vocalist and Jazz at Lincoln Center artist. Known for her dazzling bebop and swing, Gyorgy has lit up stages around the world — from Tokyo’s Cotton Club to Live From Emmett’s Place — and now she brings that same electric energy to Westport for one night only.
This is your chance to experience an international jazz sensation at the height of her career. With her 2025 JUNO-winning album Hello! How Are You? and her brand-new release Asking For Trouble, Caity delivers a performance that blends timeless swing with fresh originality. Seats are limited — secure your tickets today and be part of an unforgettable evening of world-class jazz at MoCA\CT.
Category: Classical Music.
Sunday, October 19, 2025, 4:00 PM – 5:30 PM.
19 Newtown Turnpike Westport, CT 06880.
For more info visit mocact.org. Free Stop the Bleed Class
STOP THE BLEED® Certification Class:
The American College of Surgeons’ STOP THE BLEED® program turns ordinary bystanders into immediate responders, giving you the skills to control life‑threatening bleeding before professional help arrives - at home, at work, or on the road.
In just 90 minutes you’ll learn—and practice—the three proven techniques that save lives:
Apply focused pressure to the wound
Pack and compress deep injuries
Apply a tourniquet correctly and safely.
Category: Education.
Wednesday, October 22, 2025, 7:00 PM – 8:30 PM.
Westport Volunteer EMS Headquarters: 50 Jesup Road, Westport, CT.
For more info visit www.westportems.org. Westport Farmers Market
Under the leadership of our Executive Director, Lori Cochran-Dougall, the Westport Farmers’ Market is recognized in Connecticut for its leadership in implementing the highest vendor standards and guidelines in the state, curating meaningful community outreach and programming and elevating environmental standards within this farmers' market and beyond. The market’s entrenchment in the community of outstanding chefs coupled with engaged corporate and community sponsors makes the Westport Farmers’ Market the central hub of the food community in Fairfield County and beyond. With 50+ highly curated vendors, we welcome thousands of shoppers into our community every week.
Come see what all of the talk is about!
Category: Community. Fair/Festival. Music. Outdoors/Recreation. Seasonal.
Thursday, October 23, 2025, 10:00 AM – 2:00 PM.
50 Imperial Avenue, Westport.
For more info visit www.westportfarmersmarket.com. WESTPORT WOMAN'S CLUB EPIC CLOTHING SALE
See flyer for times.
Category: Fundraising Events.
Friday, October 24, 2025, 10:00 AM – Sunday, October 26, 2025, 4:00 PM.
44 IMPERIAL AVE.
Julian Shively & Emma McDonald: An evening of jazz, R&B and neo-soul
Montreal-based jazz pianist Julian Shively is returning to Connecticut for a show in Westport - not to be missed! ♫
Julian’s a remarkable musician, equally at home on the cello, classical piano, and jazz piano. He’s now honing his focus on jazz, where his artistry continues to shine. His musicianship is deeply expressive and now collaborates with singer Emma McDonald, a dynamic and soulful vocalist. Together, they bring a captivating mix of jazz, R&B, and neo-soul, and have been earning enthusiastic responses wherever they perform.
~ Reception to follow ~
TICKETS $20 via Venmo - https://account.venmo.com/u/Tanya-Shively-1
Please indicate name and either phone or email for ticket confirmation.
TICKETS are also available on Eventbrite:
https://www.eventbrite.com/e/julian-shively-emma-mcdonald-an-evening-of-jazz-rb-and-neo-soul-tickets-1625371101719?aff=oddtdtcreator.
Category: Music. Other.
Friday, October 24, 2025, 7:00 PM – 8:30 PM.
Suzuki Music School
246 Post Road East, Westport, CT 06880.
For more info visit www.facebook.com. Pumpkin Carving & Painting
Earthplace will supply all the materials and handle the cleanup for easy pumpkin decorating and carving. Leftover pumpkins will be composted or fed to our animals.
$30 reserves one pumpkin and a table for up to 2 adults and 3 kids.
A limited number of additional pumpkins may be available for a suggested donation of $5 each. Guests may also bring their own pumpkins.
Category: Children and Families. Community. Visual Arts. Seasonal. Outdoors/Recreation. Hobbies.
Sunday, October 26, 2025, 12:00 PM – 2:00 PM.
Earthplace
10 Woodside Lane
Westport, CT.
For more info visit earthplace.app.neoncrm.com. League of Women Voters of Westport Debates
League of Women Voters Local Candidates Debates. The League of Women Voters is a nonpartisan organization encouraging informed and active participation in government. It influences public policy through education and advocacy.
Category: Community. Other.
Monday, October 27, 2025, 6:30 PM – 8:45 PM.
Westport Library, 20 Jesup Rd, Westport.
For more info visit www.lwvwestport.org. League of Women Voters of Westport Debates
League of Women Voters Local Candidates Debates. The League of Women Voters is a nonpartisan organization encouraging informed and active participation in government. It influences public policy through education and advocacy.
Category: Community. Other.
Tuesday, October 28, 2025, 6:30 PM – 8:45 PM.
Westport Library, 20 Jesup Rd, Westport.
For more info visit www.lwvwestport.org. The Importance of Being Earnest
Oscar Wilde's famous comedy! Mistaken identities, secret engagements, a lost handbag, and one very formidable aunt set the stage for this classic, fast-paced romp through Victorian society. Two wildly eligible bachelors bend the truth in their pursuit of love, only to land in a web of hilarious complications. Full of razor-sharp wit and larger-than-life characters, this sparkling satire gleefully skewers love, marriage, and high society. Wilde’s gift for language and outrageous humor is on full display in this joyously theatrical masterpiece.
Category: Theater.
Tuesday, October 28, 2025, 7:00 PM – 9:00 PM.
Westport Country Playhouse.
For more info visit www.westportplayhouse.org. The Importance of Being Earnest
Oscar Wilde's famous comedy! Mistaken identities, secret engagements, a lost handbag, and one very formidable aunt set the stage for this classic, fast-paced romp through Victorian society. Two wildly eligible bachelors bend the truth in their pursuit of love, only to land in a web of hilarious complications. Full of razor-sharp wit and larger-than-life characters, this sparkling satire gleefully skewers love, marriage, and high society. Wilde’s gift for language and outrageous humor is on full display in this joyously theatrical masterpiece.
Category: Theater.
Wednesday, October 29, 2025, 7:00 PM – 9:00 PM.
Westport Country Playhouse.
For more info visit www.westportplayhouse.org. Westport Farmers Market
Under the leadership of our Executive Director, Lori Cochran-Dougall, the Westport Farmers’ Market is recognized in Connecticut for its leadership in implementing the highest vendor standards and guidelines in the state, curating meaningful community outreach and programming and elevating environmental standards within this farmers' market and beyond. The market’s entrenchment in the community of outstanding chefs coupled with engaged corporate and community sponsors makes the Westport Farmers’ Market the central hub of the food community in Fairfield County and beyond. With 50+ highly curated vendors, we welcome thousands of shoppers into our community every week.
Come see what all of the talk is about!
Category: Community. Fair/Festival. Music. Outdoors/Recreation. Seasonal.
Thursday, October 30, 2025, 10:00 AM – 2:00 PM.
50 Imperial Avenue, Westport.
For more info visit www.westportfarmersmarket.com. The Importance of Being Earnest
Oscar Wilde's famous comedy! Mistaken identities, secret engagements, a lost handbag, and one very formidable aunt set the stage for this classic, fast-paced romp through Victorian society. Two wildly eligible bachelors bend the truth in their pursuit of love, only to land in a web of hilarious complications. Full of razor-sharp wit and larger-than-life characters, this sparkling satire gleefully skewers love, marriage, and high society. Wilde’s gift for language and outrageous humor is on full display in this joyously theatrical masterpiece.
Category: Theater.
Thursday, October 30, 2025, 7:00 PM – 9:00 PM.
Westport Country Playhouse.
For more info visit www.westportplayhouse.org. The Importance of Being Earnest
Oscar Wilde's famous comedy! Mistaken identities, secret engagements, a lost handbag, and one very formidable aunt set the stage for this classic, fast-paced romp through Victorian society. Two wildly eligible bachelors bend the truth in their pursuit of love, only to land in a web of hilarious complications. Full of razor-sharp wit and larger-than-life characters, this sparkling satire gleefully skewers love, marriage, and high society. Wilde’s gift for language and outrageous humor is on full display in this joyously theatrical masterpiece.
Category: Theater.
Friday, October 31, 2025, 8:00 PM – 10:00 PM.
Westport Country Playhouse.
For more info visit www.westportplayhouse.org. Free First Saturdays
First Saturdays are a great opportunity to experience what we have to offer at the Westport Museum free of charge on the first Saturday of each month.
Young visitors can enjoy a scavenger hunt in the museum, the diorama of Westport featuring an audio tour by Joanne Woodward, coloring pages, colonial games and more. Adult visitors will enjoy our wide array of exhibits. Our 2025 exhibition, Playful Pastimes 1890-1910, is on view as well as our local history gallery
More info below:
https://westporthistory.org/event/free-first-saturdays-2/2025-01-04/
Westport Museum is accessible via public transit! The Westport-Saugatuck railroad station has connections on the MTA New Haven line from Norwalk, Bridgeport, Stratford, Milford, and New Haven, and more. Uber 2.3 miles to the Museum or take the Norwalk Wheels bus transit system when available to Post Road West at Myrtle Avenue, which is a brief 7-minute walk from the Museum!
Park on Myrtle Avenue and Avery Place or behind Westport Town Hall or…
Category: Children and Families.
Saturday, November 1, 2025, 11:00 AM – 5:00 PM.
Westport Museum.
Emma's Revolution
On Saturday evening, December 6th at 8:00pm the award-winning Emma’s Revolution will be live at Voices Cafe.
Known for fearless, truth-telling lyrics and melodies you can't resist singing, Pat Humphries & Sandy O’s artistry features soaring harmonies and lush acoustic instruments, in songs that span folk to jazz and funk to rock. This activist duo’s message is strong, their talent is timeless, you don’t want to miss them!
For tickets go to: voicescafe.org.
Doors open at 7:30pm, with showtime at 8:00pm. Tickets and information are available at voicescafe.org. General admission is $25 per ticket.
Voices Cafe offers a BYO setting with a choice of coffee-house style seating at tables or individual seating, and guests are welcome to bring their own beverages and snacks. Groups of four or more can reserve table space.
Voices Cafe concerts support social justice programs in our local community and are presented at The Unitarian Universalist Congregation in Westport at 10 Lyons Plains Road, Westport CT.
Category: Music.
Saturday, November 1, 2025, 8:00 PM – 10:30 PM.
For more info visit voicescafe.org. The Importance of Being Earnest
Oscar Wilde's famous comedy! Mistaken identities, secret engagements, a lost handbag, and one very formidable aunt set the stage for this classic, fast-paced romp through Victorian society. Two wildly eligible bachelors bend the truth in their pursuit of love, only to land in a web of hilarious complications. Full of razor-sharp wit and larger-than-life characters, this sparkling satire gleefully skewers love, marriage, and high society. Wilde’s gift for language and outrageous humor is on full display in this joyously theatrical masterpiece.
Category: Theater.
Saturday, November 1, 2025, 8:00 PM – 10:00 PM.
Westport Country Playhouse.
For more info visit www.westportplayhouse.org. Winged Wonders
First Sunday of the month, 1pm. Experience our birds of prey outside their enclosures! On the first Sunday of the month we host a bird-on-glove demonstration where you can learn all about some of our magnificent raptors. Naturalists will discuss the animals' traits, behaviors, and unique characteristics while the birds interact with their handlers.
FREE with admission to Earthplace!
Category: Children and Families. Education. Lectures, Presentations, Workshops.
Sunday, November 2, 2025, 1:00 PM.
Earthplace, 10 Woodside Lane, Westport, CT 06880.
For more info visit earthplace.org. The Importance of Being Earnest
Oscar Wilde's famous comedy! Mistaken identities, secret engagements, a lost handbag, and one very formidable aunt set the stage for this classic, fast-paced romp through Victorian society. Two wildly eligible bachelors bend the truth in their pursuit of love, only to land in a web of hilarious complications. Full of razor-sharp wit and larger-than-life characters, this sparkling satire gleefully skewers love, marriage, and high society. Wilde’s gift for language and outrageous humor is on full display in this joyously theatrical masterpiece.
Category: Theater.
Sunday, November 2, 2025, 3:00 PM – 5:00 PM.
Westport Country Playhouse.
For more info visit www.westportplayhouse.org. The Importance of Being Earnest
Oscar Wilde's famous comedy! Mistaken identities, secret engagements, a lost handbag, and one very formidable aunt set the stage for this classic, fast-paced romp through Victorian society. Two wildly eligible bachelors bend the truth in their pursuit of love, only to land in a web of hilarious complications. Full of razor-sharp wit and larger-than-life characters, this sparkling satire gleefully skewers love, marriage, and high society. Wilde’s gift for language and outrageous humor is on full display in this joyously theatrical masterpiece.
Category: Theater.
Tuesday, November 4, 2025, 7:00 PM – 9:00 PM.
Westport Country Playhouse.
For more info visit www.westportplayhouse.org. The Importance of Being Earnest
Oscar Wilde's famous comedy! Mistaken identities, secret engagements, a lost handbag, and one very formidable aunt set the stage for this classic, fast-paced romp through Victorian society. Two wildly eligible bachelors bend the truth in their pursuit of love, only to land in a web of hilarious complications. Full of razor-sharp wit and larger-than-life characters, this sparkling satire gleefully skewers love, marriage, and high society. Wilde’s gift for language and outrageous humor is on full display in this joyously theatrical masterpiece.
Category: Theater.
Wednesday, November 5, 2025, 2:00 PM – 4:00 PM.
Westport Country Playhouse.
For more info visit www.westportplayhouse.org. The Importance of Being Earnest
Oscar Wilde's famous comedy! Mistaken identities, secret engagements, a lost handbag, and one very formidable aunt set the stage for this classic, fast-paced romp through Victorian society. Two wildly eligible bachelors bend the truth in their pursuit of love, only to land in a web of hilarious complications. Full of razor-sharp wit and larger-than-life characters, this sparkling satire gleefully skewers love, marriage, and high society. Wilde’s gift for language and outrageous humor is on full display in this joyously theatrical masterpiece.
Category: Theater.
Wednesday, November 5, 2025, 7:00 PM – 9:00 PM.
Westport Country Playhouse.
For more info visit www.westportplayhouse.org. Westport Farmers Market
Under the leadership of our Executive Director, Lori Cochran-Dougall, the Westport Farmers’ Market is recognized in Connecticut for its leadership in implementing the highest vendor standards and guidelines in the state, curating meaningful community outreach and programming and elevating environmental standards within this farmers' market and beyond. The market’s entrenchment in the community of outstanding chefs coupled with engaged corporate and community sponsors makes the Westport Farmers’ Market the central hub of the food community in Fairfield County and beyond. With 50+ highly curated vendors, we welcome thousands of shoppers into our community every week.
Come see what all of the talk is about!
Category: Community. Fair/Festival. Music. Outdoors/Recreation. Seasonal.
Thursday, November 6, 2025, 10:00 AM – 2:00 PM.
50 Imperial Avenue, Westport.
For more info visit www.westportfarmersmarket.com. The Importance of Being Earnest
Oscar Wilde's famous comedy! Mistaken identities, secret engagements, a lost handbag, and one very formidable aunt set the stage for this classic, fast-paced romp through Victorian society. Two wildly eligible bachelors bend the truth in their pursuit of love, only to land in a web of hilarious complications. Full of razor-sharp wit and larger-than-life characters, this sparkling satire gleefully skewers love, marriage, and high society. Wilde’s gift for language and outrageous humor is on full display in this joyously theatrical masterpiece.
Category: Theater.
Thursday, November 6, 2025, 7:00 PM – 9:00 PM.
Westport Country Playhouse.
For more info visit www.westportplayhouse.org. The Importance of Being Earnest
Oscar Wilde's famous comedy! Mistaken identities, secret engagements, a lost handbag, and one very formidable aunt set the stage for this classic, fast-paced romp through Victorian society. Two wildly eligible bachelors bend the truth in their pursuit of love, only to land in a web of hilarious complications. Full of razor-sharp wit and larger-than-life characters, this sparkling satire gleefully skewers love, marriage, and high society. Wilde’s gift for language and outrageous humor is on full display in this joyously theatrical masterpiece.
Category: Theater.
Friday, November 7, 2025, 8:00 PM – 10:00 PM.
Westport Country Playhouse.
For more info visit www.westportplayhouse.org. The Importance of Being Earnest
Oscar Wilde's famous comedy! Mistaken identities, secret engagements, a lost handbag, and one very formidable aunt set the stage for this classic, fast-paced romp through Victorian society. Two wildly eligible bachelors bend the truth in their pursuit of love, only to land in a web of hilarious complications. Full of razor-sharp wit and larger-than-life characters, this sparkling satire gleefully skewers love, marriage, and high society. Wilde’s gift for language and outrageous humor is on full display in this joyously theatrical masterpiece.
Category: Theater.
Saturday, November 8, 2025, 3:00 PM – 5:00 PM.
Westport Country Playhouse.
For more info visit www.westportplayhouse.org. Mark Naftalin & Friends Blues Show
BLUES ICON ANNOUNCES SHOW IN WESTPORT, CT!!
We are delighted to announce that Mark Naftalin & Friends are coming to VFW Westport on Saturday November 8th, 2025! Noted keyboardist, producer and radio host, Mr Naftalin rose to international renown as the keyboardist with the influential Paul Butterfield Blues Band, with whom he was inducted into the Rock and Roll Hall of Fame in 2015.
For this appearance, Naftlain's band of "Friends" features guitarist/vocalist Paul Gabriel (Blue In The Face, Paul Gabriel Blues Band, Connecticut Blues Society Lifetime Achievement Award); singing harmonicist Mark Zaretsky (Cobalt Rhythm Kings, The Chicago Dawgs/Finalist 2025 Connecticut Blues Challenge) and guitarist/vocalist JD Seem (Faster Things - Allman Brothers Tribute, Southern Fried, JDs Jam at The Granite).
Pathbreakers in the 1960s blues boom, the inter-racial Butterfield Band opened doors for blues masters like B.B. King and Muddy Waters, and Naftalin went on to record and/or concertize with a host of blues stars, in…
Category: Music.
Saturday, November 8, 2025, 7:00 PM – 11:00 PM.
VFW Westport.
For more info visit www.ticketleap.events. The Importance of Being Earnest
Oscar Wilde's famous comedy! Mistaken identities, secret engagements, a lost handbag, and one very formidable aunt set the stage for this classic, fast-paced romp through Victorian society. Two wildly eligible bachelors bend the truth in their pursuit of love, only to land in a web of hilarious complications. Full of razor-sharp wit and larger-than-life characters, this sparkling satire gleefully skewers love, marriage, and high society. Wilde’s gift for language and outrageous humor is on full display in this joyously theatrical masterpiece.
Category: Theater.
Saturday, November 8, 2025, 8:00 PM – 10:00 PM.
Westport Country Playhouse.
For more info visit www.westportplayhouse.org. The Importance of Being Earnest
Oscar Wilde's famous comedy! Mistaken identities, secret engagements, a lost handbag, and one very formidable aunt set the stage for this classic, fast-paced romp through Victorian society. Two wildly eligible bachelors bend the truth in their pursuit of love, only to land in a web of hilarious complications. Full of razor-sharp wit and larger-than-life characters, this sparkling satire gleefully skewers love, marriage, and high society. Wilde’s gift for language and outrageous humor is on full display in this joyously theatrical masterpiece.
Category: Theater.
Sunday, November 9, 2025, 3:00 PM – 5:00 PM.
Westport Country Playhouse.
For more info visit www.westportplayhouse.org. The Importance of Being Earnest
Oscar Wilde's famous comedy! Mistaken identities, secret engagements, a lost handbag, and one very formidable aunt set the stage for this classic, fast-paced romp through Victorian society. Two wildly eligible bachelors bend the truth in their pursuit of love, only to land in a web of hilarious complications. Full of razor-sharp wit and larger-than-life characters, this sparkling satire gleefully skewers love, marriage, and high society. Wilde’s gift for language and outrageous humor is on full display in this joyously theatrical masterpiece.
Category: Theater.
Wednesday, November 12, 2025, 7:00 PM – 9:00 PM.
Westport Country Playhouse.
For more info visit www.westportplayhouse.org. Westport Farmers Market
Under the leadership of our Executive Director, Lori Cochran-Dougall, the Westport Farmers’ Market is recognized in Connecticut for its leadership in implementing the highest vendor standards and guidelines in the state, curating meaningful community outreach and programming and elevating environmental standards within this farmers' market and beyond. The market’s entrenchment in the community of outstanding chefs coupled with engaged corporate and community sponsors makes the Westport Farmers’ Market the central hub of the food community in Fairfield County and beyond. With 50+ highly curated vendors, we welcome thousands of shoppers into our community every week.
Come see what all of the talk is about!
Category: Community. Fair/Festival. Music. Outdoors/Recreation. Seasonal.
Thursday, November 13, 2025, 10:00 AM – 2:00 PM.
50 Imperial Avenue, Westport.
For more info visit www.westportfarmersmarket.com. Staples Players Les Miserables Performance
Staples Players perform the high school edition of Les Miserables.
Category: Theater.
Thursday, November 13, 2025, 7:00 PM – 9:00 PM.
Staples High School.
For more info visit www.staplesplayers.com. The Importance of Being Earnest
Oscar Wilde's famous comedy! Mistaken identities, secret engagements, a lost handbag, and one very formidable aunt set the stage for this classic, fast-paced romp through Victorian society. Two wildly eligible bachelors bend the truth in their pursuit of love, only to land in a web of hilarious complications. Full of razor-sharp wit and larger-than-life characters, this sparkling satire gleefully skewers love, marriage, and high society. Wilde’s gift for language and outrageous humor is on full display in this joyously theatrical masterpiece.
Category: Theater.
Thursday, November 13, 2025, 7:00 PM – 9:00 PM.
Westport Country Playhouse.
For more info visit www.westportplayhouse.org. Staples Players Les Miserables Performance
Staples Players perform the high school edition of Les Miserables.
Category: Theater.
Friday, November 14, 2025, 7:00 PM – 9:00 PM.
Staples High School.
For more info visit www.staplesplayers.com. The Importance of Being Earnest
Oscar Wilde's famous comedy! Mistaken identities, secret engagements, a lost handbag, and one very formidable aunt set the stage for this classic, fast-paced romp through Victorian society. Two wildly eligible bachelors bend the truth in their pursuit of love, only to land in a web of hilarious complications. Full of razor-sharp wit and larger-than-life characters, this sparkling satire gleefully skewers love, marriage, and high society. Wilde’s gift for language and outrageous humor is on full display in this joyously theatrical masterpiece.
Category: Theater.
Friday, November 14, 2025, 8:00 PM – 10:00 PM.
Westport Country Playhouse.
For more info visit www.westportplayhouse.org. Staples Players Les Miserables Performance
Staples Players perform the high school edition of Les Miserables.
Category: Theater.
Saturday, November 15, 2025, 2:00 PM – 4:00 PM.
Staples High School.
For more info visit www.staplesplayers.com. The Importance of Being Earnest
Oscar Wilde's famous comedy! Mistaken identities, secret engagements, a lost handbag, and one very formidable aunt set the stage for this classic, fast-paced romp through Victorian society. Two wildly eligible bachelors bend the truth in their pursuit of love, only to land in a web of hilarious complications. Full of razor-sharp wit and larger-than-life characters, this sparkling satire gleefully skewers love, marriage, and high society. Wilde’s gift for language and outrageous humor is on full display in this joyously theatrical masterpiece.
Category: Theater.
Saturday, November 15, 2025, 3:00 PM – 5:00 PM.
Westport Country Playhouse.
For more info visit www.westportplayhouse.org. Staples Players Les Miserables Performance
Staples Players perform the high school edition of Les Miserables.
Category: Theater.
Saturday, November 15, 2025, 7:00 PM – 9:00 PM.
Staples High School.
For more info visit www.staplesplayers.com. The Importance of Being Earnest
Oscar Wilde's famous comedy! Mistaken identities, secret engagements, a lost handbag, and one very formidable aunt set the stage for this classic, fast-paced romp through Victorian society. Two wildly eligible bachelors bend the truth in their pursuit of love, only to land in a web of hilarious complications. Full of razor-sharp wit and larger-than-life characters, this sparkling satire gleefully skewers love, marriage, and high society. Wilde’s gift for language and outrageous humor is on full display in this joyously theatrical masterpiece.
Category: Theater.
Saturday, November 15, 2025, 8:00 PM – 10:00 PM.
Westport Country Playhouse.
For more info visit www.westportplayhouse.org. Staples Players Les Miserables Performance
Staples Players perform the high school edition of Les Miserables.
Category: Theater.
Sunday, November 16, 2025, 2:00 PM – 4:00 PM.
Staples High School.
For more info visit www.staplesplayers.com. Westport Farmers Market
Under the leadership of our Executive Director, Lori Cochran-Dougall, the Westport Farmers’ Market is recognized in Connecticut for its leadership in implementing the highest vendor standards and guidelines in the state, curating meaningful community outreach and programming and elevating environmental standards within this farmers' market and beyond. The market’s entrenchment in the community of outstanding chefs coupled with engaged corporate and community sponsors makes the Westport Farmers’ Market the central hub of the food community in Fairfield County and beyond. With 50+ highly curated vendors, we welcome thousands of shoppers into our community every week.
Come see what all of the talk is about!
Category: Community. Fair/Festival. Music. Outdoors/Recreation. Seasonal.
Thursday, November 20, 2025, 10:00 AM – 2:00 PM.
7 Sylvan Ln, Westport.
For more info visit www.westportfarmersmarket.com. Staples Players Les Miserables Performance
Staples Players perform the high school edition of Les Miserables.
Category: Theater.
Thursday, November 20, 2025, 7:00 PM – 9:00 PM.
Staples High School.
For more info visit www.staplesplayers.com. Free QPR Suicide Prevention Training
Question-Persuade-Refer (QPR) is an evidence-based training for the general public (ages 16+). We encourage everyone to receive the training! Learn how to reach out to someone who may be struggling and provide life-saving support. The training includes videos, a slideshow, and a group role play.
For 2025, we are offering this training for free bimonthly on last Fridays from 12-1:30pm. Please note that at least 5 attendees are required for a training to take place. We also ask you not to attend any suicide prevention training if you have been personally affected by suicide in the past 6 months.
We offer QPR group trainings to organizations in our catchment area upon request (English or Spanish), as well as other training programs. Please email Margaret at mwatt@positivedirections.org if interested in this option.
RSVP via the web link!
Category: Education. Lectures, Presentations, Workshops.
Friday, November 21, 2025, 12:00 PM – 1:30 PM.
Positive Directions, 90 Post Rd W, Westport, CT 06880.
For more info visit www.positivedirections.org. Staples Players Les Miserables Performance
Staples Players perform the high school edition of Les Miserables.
Category: Theater.
Friday, November 21, 2025, 7:00 PM – 9:00 PM.
Staples High School.
For more info visit www.staplesplayers.com. Mandy Patinkin in Concert: Jukebox
Tony-winning Broadway legend, Emmy-winning TV star, renowned for creating timeless characters in movies such as The Princess Bride, Yentl, and Dick Tracy — Mandy Patinkin presents his new show, Mandy Patinkin in Concert: JUKEBOX.
With Adam Ben-David on piano, JUKEBOX features Mandy’s own hand-picked collection of classic musical numbers, expressed as only he can through a unique mastery of word and song. An unparalleled body of work from one of North America’s preeminent entertainers.
Category: Music.
Friday, November 21, 2025, 8:00 PM – 9:30 PM.
Westport Country Playhouse.
For more info visit www.westportplayhouse.org. Staples Players Les Miserables Performance
Staples Players perform the high school edition of Les Miserables.
Category: Theater.
Saturday, November 22, 2025, 2:00 PM – 4:00 PM.
Staples High School.
For more info visit www.staplesplayers.com. Staples Players Les Miserables Performance
Staples Players perform the high school edition of Les Miserables.
Category: Theater.
Saturday, November 22, 2025, 7:00 PM – 9:00 PM.
Staples High School.
For more info visit www.staplesplayers.com. Staples Players Les Miserables Performance
Staples Players perform the high school edition of Les Miserables.
Category: Theater.
Sunday, November 23, 2025, 2:00 PM – 4:00 PM.
Staples High School.
For more info visit www.staplesplayers.com. Westport Farmers Market
Under the leadership of our Executive Director, Lori Cochran-Dougall, the Westport Farmers’ Market is recognized in Connecticut for its leadership in implementing the highest vendor standards and guidelines in the state, curating meaningful community outreach and programming and elevating environmental standards within this farmers' market and beyond. The market’s entrenchment in the community of outstanding chefs coupled with engaged corporate and community sponsors makes the Westport Farmers’ Market the central hub of the food community in Fairfield County and beyond. With 50+ highly curated vendors, we welcome thousands of shoppers into our community every week.
Come see what all of the talk is about!
Category: Community. Fair/Festival. Music. Outdoors/Recreation. Seasonal.
Thursday, November 27, 2025, 10:00 AM – 2:00 PM.
7 Sylvan Ln, Westport.
For more info visit www.westportfarmersmarket.com. Westport Farmers Market
Under the leadership of our Executive Director, Lori Cochran-Dougall, the Westport Farmers’ Market is recognized in Connecticut for its leadership in implementing the highest vendor standards and guidelines in the state, curating meaningful community outreach and programming and elevating environmental standards within this farmers' market and beyond. The market’s entrenchment in the community of outstanding chefs coupled with engaged corporate and community sponsors makes the Westport Farmers’ Market the central hub of the food community in Fairfield County and beyond. With 50+ highly curated vendors, we welcome thousands of shoppers into our community every week.
Come see what all of the talk is about!
Category: Community. Fair/Festival. Music. Outdoors/Recreation. Seasonal.
Thursday, December 4, 2025, 10:00 AM – 2:00 PM.
7 Sylvan Ln, Westport.
For more info visit www.westportfarmersmarket.com. Free First Saturdays
First Saturdays are a great opportunity to experience what we have to offer at the Westport Museum free of charge on the first Saturday of each month.
Young visitors can enjoy a scavenger hunt in the museum, the diorama of Westport featuring an audio tour by Joanne Woodward, coloring pages, colonial games and more. Adult visitors will enjoy our wide array of exhibits. Our 2025 exhibition, Playful Pastimes 1890-1910, is on view as well as our local history gallery
More info below:
https://westporthistory.org/event/free-first-saturdays-2/2025-01-04/
Westport Museum is accessible via public transit! The Westport-Saugatuck railroad station has connections on the MTA New Haven line from Norwalk, Bridgeport, Stratford, Milford, and New Haven, and more. Uber 2.3 miles to the Museum or take the Norwalk Wheels bus transit system when available to Post Road West at Myrtle Avenue, which is a brief 7-minute walk from the Museum!
Park on Myrtle Avenue and Avery Place or behind Westport Town Hall or…
Category: Children and Families.
Saturday, December 6, 2025, 11:00 AM – 5:00 PM.
Westport Museum.
On The Trail
On Saturday evening, December 6th at 8:00pm Voices Cafe will be rocking with On The Trail, a modern acoustic band that explores everything from bluegrass to contemporary pop, from stunning instrumentals to beautiful traditional songs.
On The Trail features Austin Scelzo (fiddle and vocals), Tom Polizzi (mandolin and vocals), Charlie Widmer (guitar and vocals) and Matt Curley (upright bass and vocals).
For tickets go to: voicescafe.org. Doors open at 7:30pm, with showtime at 8:00pm. Tickets and information are available at voicescafe.org. General admission is $25 per ticket.
Voices Cafe offers a BYO setting with a choice of coffee-house style seating at tables or individual seating, and guests are welcome to bring their own beverages and snacks. Groups of four or more can reserve table space.
Voices Cafe concerts support social justice programs in our local community and are presented at The Unitarian Universalist Congregation in Westport, at 10 Lyons Plains Road.
Category: Music.
Saturday, December 6, 2025, 8:00 PM – 10:30 PM.
Voices Cafe
10 Lyons Plains Road, Westport CT 06880.
For more info visit voicescafe.org. Winged Wonders
First Sunday of the month, 1pm. Experience our birds of prey outside their enclosures! On the first Sunday of the month we host a bird-on-glove demonstration where you can learn all about some of our magnificent raptors. Naturalists will discuss the animals' traits, behaviors, and unique characteristics while the birds interact with their handlers.
FREE with admission to Earthplace!
Category: Children and Families. Education. Lectures, Presentations, Workshops.
Sunday, December 7, 2025, 1:00 PM.
Earthplace, 10 Woodside Lane, Westport, CT 06880.
For more info visit earthplace.org. Westport Farmers Market
Under the leadership of our Executive Director, Lori Cochran-Dougall, the Westport Farmers’ Market is recognized in Connecticut for its leadership in implementing the highest vendor standards and guidelines in the state, curating meaningful community outreach and programming and elevating environmental standards within this farmers' market and beyond. The market’s entrenchment in the community of outstanding chefs coupled with engaged corporate and community sponsors makes the Westport Farmers’ Market the central hub of the food community in Fairfield County and beyond. With 50+ highly curated vendors, we welcome thousands of shoppers into our community every week.
Come see what all of the talk is about!
Category: Community. Fair/Festival. Music. Outdoors/Recreation. Seasonal.
Thursday, December 11, 2025, 10:00 AM – 2:00 PM.
7 Sylvan Ln, Westport.
For more info visit www.westportfarmersmarket.com. MoCA\CT Presents: Emmet Cohen Trio
Emmet Cohen is one of today’s most exciting jazz pianists, celebrated for his charisma, masterful playing, and the way he draws audiences into every note. A rising star who has already played the world’s great stages, Cohen brings a fresh, modern spark to the jazz tradition—making his concerts as thrilling for first-time listeners as they are for lifelong fans.
Appearing with the acclaimed Emmet Cohen Trio, he delivers a performance full of energy, soul, and playful improvisation. Known for their remarkable chemistry and engaging sound, the Trio brings the piano, bass, and drums to life in ways that are both powerful and joyful. Don’t miss this chance to experience live jazz at its very best—reserve your seats now for an unforgettable night of music.
“…supremely gifted and impassioned artist of the highest order.” – All About Jazz
MoCA\CT members receive 10% off tickets.
This is your chance to experience an international jazz sensation at the height of her career. With her 2025 JUNO-winning album He…
Category: Classical Music.
Thursday, December 11, 2025, 7:00 PM – 8:30 PM.
19 Newtown Turnpike Westport, CT 06880.
For more info visit mocact.org.