All-School Calendar

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Returning boarding students begin arriving to campus

Upper School Category: Annual Calendar: US 2025-2026. Event Type: In-person. Monday, September 1, 2025.

Labor Day

Employee Events Category: Holidays. Event Type: In-person. Monday, September 1, 2025.

Staff holiday

Employee Events Category: Faculty and Staff: LS. Faculty and Staff: MS. Faculty and Staff: US. Holidays. Event Type: In-person. Monday, September 1, 2025.

Orange week

Middle School Category: Academics. Event Type: In-person. Tuesday, September 2, 2025.

K-5 Meet the Teachers & Classroom Visits

Lower School Category: All Grades K–5. Annual Calendar: LS 2025-2026. Event Type: In-person. Tuesday, September 2, 2025.

Middle School New-to-Milton Student Orientation

Middle School Category: All Grades 6–8. Annual Calendar: MS 2025-2026. Event Type: In-person. Tuesday, September 2, 2025, 9:00 AM – 12:00 PM.

MS New-to-Milton Parent/Caregiver Coffee

Middle School Category: All Grades 6–8. Parents. Event Type: In-person. Tuesday, September 2, 2025, 9:00 AM – 10:00 AM. Ware Patio (Goodwin Room rainspace).

Kindergarten and New Grade 4 Family Orientation

Lower School Category: All Grades K–5. Annual Calendar: US 2025-2026. Event Type: In-person. Tuesday, September 2, 2025, 10:00 AM – 11:00 AM.

Orange week

Middle School Category: Academics. Event Type: In-person. Wednesday, September 3, 2025.

Upper School All Student Programming

Upper School Category: Annual Calendar: US 2025-2026. Event Type: In-person. Wednesday, September 3, 2025.

Bus service begins

Lower School Category: Academics. Annual Calendar: LS 2025-2026. Annual Calendar: MS 2025-2026. Annual Calendar: US 2025-2026. Event Type: In-person. Wednesday, September 3, 2025.

Lower School ASP begins

Lower School Category: All Grades K–5. Annual Calendar: LS 2025-2026. Event Type: In-person. Wednesday, September 3, 2025.

Lower School First full day of classes (2pm dismissal, 2:15pm buses available, ASP begins)

Lower School Category: All Grades K–5. Annual Calendar: LS 2025-2026. Event Type: In-person. Wednesday, September 3, 2025.

Middle School All Student Programming (2pm dismissal, 2:15pm buses available)

Middle School Category: All Grades 6–8. Annual Calendar: MS 2025-2026. Event Type: In-person. Wednesday, September 3, 2025, 8:00 AM – 2:00 PM.

Meet the interim Lower School Principal: Shelley Borror Jackson

Lower School Category: All Grades K–5. Parents. Event Type: In-person. Wednesday, September 3, 2025, 8:15 AM – 9:30 AM. Goodwin Room. For more info visit events.milton.edu.

Orange week

Middle School Category: Academics. Event Type: In-person. Thursday, September 4, 2025.

Upper School Classes Begin

Upper School Category: Annual Calendar: US 2025-2026. Event Type: In-person. Thursday, September 4, 2025.

Lower School classes continue (2pm dismissal, 2:15pm buses available)

Lower School Category: All Grades K–5. Annual Calendar: LS 2025-2026. Event Type: In-person. Thursday, September 4, 2025.

Middle School All Student Programming (2pm dismissal, 2:15pm buses available)

Middle School Category: All Grades 6–8. Annual Calendar: MS 2025-2026. Event Type: In-person. Thursday, September 4, 2025, 8:00 AM – 2:00 PM.

Middle School Parent/Guardian Welcome

Middle School Category: All Grades 6–8. Parents. Event Type: In-person. Thursday, September 4, 2025, 8:30 AM – 9:30 AM. Straus Library.

Field Trip (Grade 7): TreeTop Adventures

Middle School Category: All Grades 6–8. Student Activities. Event Type: In-person. Friday, September 5, 2025. Canton, MA.

Field Trip (Grade 6): Hale Education

Middle School Category: Student Activities. All Grades 6–8. Event Type: In-person. Friday, September 5, 2025. Westwood, MA.

Field Trip (Grade 8): Natick Community Organic Farm

Middle School Category: All Grades 6–8. Student Activities. Event Type: In-person. Friday, September 5, 2025. Natick, MA.

Orange week

Middle School Category: Academics. Event Type: In-person. Friday, September 5, 2025.

Lower School classes continue (2pm dismissal, 2:15pm buses available)

Lower School Category: All Grades K–5. Annual Calendar: LS 2025-2026. Event Type: In-person. Friday, September 5, 2025.

Middle School All Student Programming (2pm dismissal, 2:15pm buses available)

Middle School Category: All Grades 6–8. Annual Calendar: MS 2025-2026. Event Type: In-person. Friday, September 5, 2025, 8:00 AM – 2:00 PM.

US Quadchella

Upper School Category: Student Activities. Event Type: In-person. Friday, September 5, 2025, 7:00 PM – 10:30 PM. Quad (Rain location: Rink).

ACT Testing at Milton Academy

Upper School Category: Academics. Event Type: In-person. Saturday, September 6, 2025.

US Block Party

Upper School Category: Student Activities. Event Type: In-person. Saturday, September 6, 2025, 7:00 PM – 10:30 PM. Quad.

Blue week

Middle School Category: Academics. Event Type: In-person. Monday, September 8, 2025.

MS Afternoon Program & ASP begin

Middle School Category: Annual Calendar: MS 2025-2026. Event Type: In-person. Monday, September 8, 2025.

Spikeball Tournament

Upper School Category: Student Activities. Event Type: In-person. Friday, September 12, 2025, 6:30 PM – 8:30 PM. Quad (Rain location: ACC).

Outdoor Movie

Upper School Category: Student Activities. Event Type: In-person. Friday, September 12, 2025, 8:30 PM – 10:30 PM. Quad (Rain location: ACC).

SAT Testing at Milton Academy

Upper School Category: Academics. Event Type: In-person. Saturday, September 13, 2025.

Custom Street Signs

Upper School Category: Student Activities. Event Type: In-person. Saturday, September 13, 2025, 7:00 PM – 10:45 PM. Student Center.

Friendship Bracelet Making

Upper School Category: Student Activities. Event Type: In-person. Saturday, September 13, 2025, 7:00 PM – 10:45 PM. Student Center.

Dodgeball

Upper School Category: Student Activities. Event Type: In-person. Saturday, September 13, 2025, 8:00 PM – 10:45 PM. RSG.

Orange week

Middle School Category: Academics. Event Type: In-person. Monday, September 15, 2025.

Walter Horak '66: Go Figure sculpture exhibit

Employee Events through June 2026. Category: Arts. Event Type: In-person. Tuesday, September 16, 2025. front of AMC.

Soccer: Girls MS Orange @ Beaver

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Girls Orange. Opponent: Beaver Country Day. Wednesday, September 17, 2025, 3:15 PM – 5:45 PM. Beaver.

Soccer: Boys MS Orange vs Inly

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Boys Orange. Opponent: Inly. Wednesday, September 17, 2025, 3:30 PM. Milton.

Volleyball: MS @ BB&N

Athletics: MS Category: Athletics: MS. Team: Volleyball: MS. Opponent: BB&N. Wednesday, September 17, 2025, 3:30 PM – 5:45 PM. BB&N.

Flag Football: Boys MS vs BB&N

Athletics: MS Category: Athletics: MS. Team: Football: MS Blue. Opponent: BB&N. Wednesday, September 17, 2025, 3:45 PM. Milton.

Football: MS Orange vs BB&N

Athletics: MS Category: Athletics: MS. Team: Football: MS Orange. Opponent: BB&N. Wednesday, September 17, 2025, 3:45 PM. Milton.

Soccer: Boys MS Blue vs BB&N

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Boys Blue. Opponent: BB&N. Wednesday, September 17, 2025, 3:45 PM. Milton.

Soccer: Girls MS Blue vs BB&N

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Girls Blue. Opponent: BB&N. Wednesday, September 17, 2025, 3:45 PM. Milton.

LS Curriculum Night

Lower School Category: Annual Calendar: LS 2025-2026. Event Type: In-person. Wednesday, September 17, 2025, 6:00 PM – 8:00 PM. K-5 Classrooms & Thacher.

Club Fair

Upper School Category: Student Activities. Event Type: In-person. Thursday, September 18, 2025, 1:15 PM – 2:15 PM. ACC - Tennis Courts.

Tracy Penn: Ubiquitous - Microplastics in the Body Opening Reception

Employee Events through October 29, 2025. Category: Arts. Event Type: In-person. Thursday, September 18, 2025, 5:30 PM – 7:00 PM. Nesto Gallery.

US Speech & Debate: Yale Invitational

Upper School Category: Student Activities. Event Type: In-person. Friday, September 19, 2025 – Sunday, September 21, 2025. New Haven, CT.

Cross Country: Coed MS vs DexterSthfld / Beaver / Inly

Athletics: MS Category: Athletics: MS. Team: Cross Country: MS. Opponent: Dexter/Southfield. Friday, September 19, 2025, 3:30 PM. Milton.

Soccer: Boys MS Blue @ DexterSthfld

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Boys Blue. Opponent: Dexter/Southfield. Friday, September 19, 2025, 3:30 PM – 5:45 PM. DexterSthfld.

Soccer: Boys MS Orange @ Thayer

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Boys Orange. Opponent: Thayer. Friday, September 19, 2025, 3:30 PM – 5:45 PM. Thayer.

Soccer: Girls MS Orange @ DexterSthfld

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Girls Orange. Opponent: Dexter/Southfield. Friday, September 19, 2025, 3:30 PM – 5:45 PM. DexterSthfld.

Flag Football: Boys MS vs Rivers

Athletics: MS Category: Athletics: MS. Team: Football: MS Blue. Opponent: Rivers. Friday, September 19, 2025, 3:45 PM. Milton.

Football: MS Orange vs Rivers

Athletics: MS Category: Athletics: MS. Team: Football: MS Orange. Opponent: Rivers. Friday, September 19, 2025, 3:45 PM. Milton.

Soccer: Girls MS Blue vs Winsor

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Girls Blue. Opponent: Winsor. Friday, September 19, 2025, 3:45 PM. Milton.

Volleyball: MS vs Winsor

Athletics: MS Category: Athletics: MS. Team: Volleyball: MS. Opponent: Winsor. Friday, September 19, 2025, 3:45 PM. Milton.

US Student Activity: Mind Reader Eric Dittelman

Upper School Category: Student Activities. Event Type: In-person. Friday, September 19, 2025, 7:30 PM – 9:00 PM. King Theatre.

S'more & Music

Upper School Category: Student Activities. Event Type: In-person. Friday, September 19, 2025, 9:00 PM – 10:30 PM. Quad.

Saturday Course Session 1: Grades 5 - 8

Employee Events Category: All Grades 6–8. All Grades K–5. Academics. Event Type: In-person. Saturday, September 20, 2025.

Scavenger Hunt

Upper School Category: Student Activities. Event Type: In-person. Saturday, September 20, 2025, 7:00 PM – 8:00 PM. Meet at the Student Center.

Volleyball Under the Lights

Upper School Category: Student Activities. Event Type: In-person. Saturday, September 20, 2025, 7:30 PM – 9:30 PM. Quad (Rain location: ACC).

Felt Pennant Flags & Fudge

Upper School Category: Student Activities. Event Type: In-person. Saturday, September 20, 2025, 8:00 PM – 10:45 PM. Student Center.

LS Fall Festival

Lower School Category: All Grades K–5. Student Activities. Parents. Event Type: In-person. Sunday, September 21, 2025, 2:00 PM – 4:00 PM. JB Fields, rainspace: CSG gym.

Blue week

Middle School Category: Academics. Event Type: In-person. Monday, September 22, 2025.

Rosh Hashana begins sundown (through Wed 9/24)

Employee Events Category: Holidays. Event Type: In-person. Monday, September 22, 2025.

Rosh Hashanah (no classes)

Lower School Category: Holidays. Annual Calendar: MS 2025-2026. Annual Calendar: US 2025-2026. Annual Calendar: LS 2025-2026. Event Type: In-person. Tuesday, September 23, 2025.

Classes resume

Middle School Category: Annual Calendar: LS 2025-2026. Annual Calendar: MS 2025-2026. Annual Calendar: US 2025-2026. Event Type: In-person. Wednesday, September 24, 2025.

K-8 Admissions Tour Guide Training

Employee Events Category: All Grades 6–8. All Grades K–5. Parents. Event Type: In-person. Wednesday, September 24, 2025, 8:00 AM – 11:00 AM. Thacher Room.

Cross Country: Coed MS @ Meadowbrk / Rivers

Athletics: MS Category: Athletics: MS. Team: Cross Country: MS. Opponent: Meadowbrook. Wednesday, September 24, 2025, 3:15 PM – 5:45 PM. Meadowbrk.

Soccer: Girls MS Blue @ Derby

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Girls Blue. Opponent: Derby. Wednesday, September 24, 2025, 3:15 PM – 5:45 PM. Derby.

Field Hockey: Girls MS @ Dedham CD

Athletics: MS Category: Athletics: MS. Team: Field Hockey: MS. Opponent: Dedham Country Day. Wednesday, September 24, 2025, 3:30 PM – 5:45 PM. Dedham CD.

Soccer: Girls MS Orange vs Rivers

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Girls Orange. Opponent: Rivers. Wednesday, September 24, 2025, 3:45 PM. Milton.

Middle School Family Day

Middle School Category: All Grades 6–8. Annual Calendar: MS 2025-2026. Event Type: In-person. Friday, September 26, 2025.

Cross Country: Coed MS vs Inly

Athletics: MS Category: Athletics: MS. Team: Cross Country: MS. Opponent: Inly. Friday, September 26, 2025, 3:15 PM. Milton.

Soccer: Boys MS Orange vs DexterSthfld

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Boys Orange. Opponent: Dexter/Southfield. Friday, September 26, 2025, 3:15 PM. Milton.

Football: MS Orange vs Thayer

Athletics: MS Category: Athletics: MS. Team: Football: MS Orange. Opponent: Thayer. Friday, September 26, 2025, 3:30 PM. Milton.

Soccer: Boys MS Blue @ Roxbury Latin

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Boys Blue. Opponent: Roxbury Latin. Friday, September 26, 2025, 3:30 PM – 5:45 PM. Roxbury Latin.

Soccer: Boys MS Blue vs Thayer

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Boys Blue. Opponent: Thayer. Friday, September 26, 2025, 4:00 PM. Milton.

Soccer: Girls MS Blue @ Newton CD

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Girls Blue. Opponent: Newton Country Day. Friday, September 26, 2025, 4:00 PM – 5:45 PM. Newton CD.

Dance

Upper School Category: Student Activities. Event Type: In-person. Friday, September 26, 2025, 8:00 PM – 10:45 PM. RSG.

Saturday Course Session 1: Grades 5 - 8

Employee Events Category: All Grades 6–8. All Grades K–5. Academics. Event Type: In-person. Saturday, September 27, 2025.

Dorm Hop

Upper School Category: Student Activities. Event Type: In-person. Saturday, September 27, 2025, 7:00 PM – 8:00 PM. Starts at Hathaway.

Diamond Painting

Upper School Category: Student Activities. Event Type: In-person. Saturday, September 27, 2025, 8:00 PM – 10:45 PM. Student Center.

Flag Football Under the Lights

Upper School Category: Student Activities. Event Type: In-person. Saturday, September 27, 2025, 8:00 PM – 10:00 PM. Quad (Rain Location: ACC).

CCO College Fair

Upper School Category: College Counseling. Event Type: In-person. Sunday, September 28, 2025, 1:00 PM – 3:00 PM. Athletic & Convocation Center.

Orange week

Middle School Category: Academics. Event Type: In-person. Monday, September 29, 2025.

K-12 Programming: Hispanic & Latinx Heritage month

Employee Events Category: Academics. Event Type: In-person. Tuesday, September 30, 2025, 1:15 PM – 2:15 PM. FCC Court 1.

Cross Country: Coed MS @ Derby

Athletics: MS Category: Athletics: MS. Team: Cross Country: MS. Opponent: Derby. Tuesday, September 30, 2025, 3:15 PM – 5:45 PM. Derby.

Cross Country: Coed MS @ Derby / DexterSthfld / Lex Christian / Dana Hall

Athletics: MS Category: Athletics: MS. Team: Cross Country: MS. Opponent: Derby. Tuesday, September 30, 2025, 3:30 PM – 5:45 PM. Derby.

Soccer: Boys MS Blue @ Dedham CD

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Boys Blue. Opponent: Dedham Country Day. Tuesday, September 30, 2025, 3:30 PM – 5:45 PM. Dedham CD.

Volleyball: MS vs Dana Hall

Athletics: MS Category: Athletics: MS. Team: Volleyball: MS. Opponent: Dana Hall. Tuesday, September 30, 2025, 3:30 PM. Milton.

Yom Kippur begins sundown (through 10/2)

Employee Events Category: Holidays. Event Type: In-person. Wednesday, October 1, 2025.

Yom Kippur (no classes)

Lower School Category: Annual Calendar: US 2025-2026. Holidays. Annual Calendar: MS 2025-2026. Annual Calendar: LS 2025-2026. Event Type: In-person. Thursday, October 2, 2025.

Classes resume

Middle School Category: Annual Calendar: MS 2025-2026. Annual Calendar: LS 2025-2026. Annual Calendar: US 2025-2026. Holidays. Event Type: In-person. Friday, October 3, 2025.

Football: MS Orange @ Thayer

Athletics: MS Category: Athletics: MS. Team: Football: MS Orange. Opponent: Thayer. Friday, October 3, 2025, 3:30 PM – 5:45 PM. Thayer.

Soccer: Boys MS Blue @ Thayer

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Boys Blue. Opponent: Thayer. Friday, October 3, 2025, 3:30 PM – 5:45 PM. Thayer.

Soccer: Boys MS Orange vs BrimmerMay

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Boys Orange. Opponent: Brimmer and May. Friday, October 3, 2025, 3:30 PM. Milton.

Soccer: Girls MS Blue vs Park

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Girls Blue. Opponent: Park. Friday, October 3, 2025, 3:30 PM. Milton.

Soccer: Girls MS Orange vs DexterSthfld

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Girls Orange. Opponent: Dexter/Southfield. Friday, October 3, 2025, 3:30 PM. Milton.

Volleyball: MS @ DexterSthfld

Athletics: MS Category: Athletics: MS. Team: Volleyball: MS. Opponent: Dexter/Southfield. Friday, October 3, 2025, 3:30 PM – 5:45 PM. DexterSthfld.

Flag Football: Boys MS @ Shady Hill

Athletics: MS Category: Athletics: MS. Team: Football: MS Blue. Opponent: Shady Hill. Friday, October 3, 2025, 3:45 PM – 5:45 PM. Shady Hill.

Saturday Course Session 1: Grades 5 - 8

Employee Events Category: All Grades 6–8. All Grades K–5. Academics. Event Type: In-person. Saturday, October 4, 2025.

Blue week

Middle School Category: Academics. Event Type: In-person. Monday, October 6, 2025.

LS Picture Day

Lower School Category: All Grades K–5. Event Type: In-person. Monday, October 6, 2025.

Sukkot begins sundown (through Oct 13)

Employee Events Category: Holidays. Event Type: In-person. Monday, October 6, 2025.

K-12 Mid Autumn Festival

Lower School Category: Academics. Student Activities. Parents. Event Type: In-person. Monday, October 6, 2025, 6:00 PM – 8:30 PM. Goodwin Room.

Middle School Picture Day

Middle School Category: All Grades 6–8. Annual Calendar: MS 2025-2026. Event Type: In-person. Tuesday, October 7, 2025.

Field Hockey: Girls MS vs Derby

Athletics: MS Category: Athletics: MS. Team: Field Hockey: MS. Opponent: Derby. Wednesday, October 8, 2025, 3:15 PM. milton.

Cross Country: Coed MS vs Inly / Dedham CD

Athletics: MS Category: Athletics: MS. Team: Cross Country: MS. Opponent: Inly. Wednesday, October 8, 2025, 3:30 PM. milton.

Flag Football: Boys MS vs Dedham CD

Athletics: MS Category: Athletics: MS. Team: Football: MS Blue. Opponent: Dedham Country Day. Wednesday, October 8, 2025, 3:30 PM. milton.

Football: MS Orange vs Dedham CD

Athletics: MS Category: Athletics: MS. Team: Football: MS Orange. Opponent: Dedham Country Day. Wednesday, October 8, 2025, 3:30 PM. milton.

Soccer: Girls MS Blue @ Dedham CD

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Girls Blue. Opponent: Dedham Country Day. Wednesday, October 8, 2025, 3:30 PM – 5:45 PM. Dedham CD.

Soccer: Girls MS Orange @ Fay

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Girls Orange. Opponent: Fay. Wednesday, October 8, 2025, 3:30 PM – 5:45 PM. Fay.

Volleyball: MS vs Meadowbrk

Athletics: MS Category: Athletics: MS. Team: Volleyball: MS. Opponent: Meadowbrook. Wednesday, October 8, 2025, 3:30 PM. milton.

Soccer: Boys MS Orange vs Rivers

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Boys Orange. Opponent: Rivers. Wednesday, October 8, 2025, 3:45 PM. milton.

Flag Football: Boys MS @ Beaver

Athletics: MS Category: Athletics: MS. Team: Football: MS Blue. Opponent: Beaver Country Day. Friday, October 10, 2025, 3:30 PM – 5:45 PM. Beaver.

Soccer: Boys MS Blue vs Beaver

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Boys Blue. Opponent: Beaver Country Day. Friday, October 10, 2025, 3:30 PM. milton.

Volleyball: MS vs Beaver

Athletics: MS Category: Athletics: MS. Team: Volleyball: MS. Opponent: Beaver Country Day. Friday, October 10, 2025, 3:30 PM. milton.

K-12 Shabbat Dinner

Middle School Category: Community Engagement. Event Type: In-person. Friday, October 10, 2025, 6:00 PM – 8:30 PM. Straus Library.

Indigenous Peoples' Day (no classes)

Middle School Category: Annual Calendar: LS 2025-2026. Annual Calendar: MS 2025-2026. Annual Calendar: US 2025-2026. Holidays. Event Type: In-person. Monday, October 13, 2025.

Staff holiday

Employee Events Category: Holidays. Faculty and Staff: LS. Faculty and Staff: MS. Faculty and Staff: US. Event Type: In-person. Monday, October 13, 2025.

Classes resume

Middle School Category: Annual Calendar: LS 2025-2026. Annual Calendar: MS 2025-2026. Annual Calendar: US 2025-2026. Event Type: In-person. Tuesday, October 14, 2025.

Orange week

Middle School Category: Academics. Event Type: In-person. Tuesday, October 14, 2025.

K-12 Programming: Indigenous People’s Day

Employee Events Category: Academics. Event Type: In-person. Tuesday, October 14, 2025, 1:15 PM – 2:15 PM. FCC Court 1.

Community Engagement Day for Classes III & IV

Upper School Category: Academics. Event Type: In-person. Wednesday, October 15, 2025.

PSAT Testing for Class II Milton Academy students only

Upper School Category: Academics. Event Type: In-person. Wednesday, October 15, 2025.

SAT Testing for Class I Milton Academy students only

Upper School Category: Academics. Event Type: In-person. Wednesday, October 15, 2025.

Soccer: Boys MS Orange @ Derby

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Boys Orange. Opponent: Derby. Wednesday, October 15, 2025, 3:15 PM – 5:45 PM. Derby.

Cross Country: Coed MS @ BB&N

Athletics: MS Category: Athletics: MS. Team: Cross Country: MS. Opponent: BB&N. Wednesday, October 15, 2025, 3:30 PM – 5:45 PM. BB&N.

Flag Football: Boys MS @ BB&N

Athletics: MS Category: Athletics: MS. Team: Football: MS Blue. Opponent: BB&N. Wednesday, October 15, 2025, 3:30 PM – 5:45 PM. BB&N.

Football: MS Orange @ BB&N

Athletics: MS Category: Athletics: MS. Team: Football: MS Orange. Opponent: BB&N. Wednesday, October 15, 2025, 3:30 PM – 5:45 PM. BB&N.

Soccer: Boys MS Blue vs DexterSthfld

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Boys Blue. Opponent: Dexter/Southfield. Wednesday, October 15, 2025, 3:30 PM. milton.

Soccer: Girls MS Orange @ Winsor

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Girls Orange. Opponent: Winsor. Wednesday, October 15, 2025, 3:30 PM – 5:45 PM. Winsor.

Volleyball: MS vs DexterSthfld

Athletics: MS Category: Athletics: MS. Team: Volleyball: MS. Opponent: Dexter/Southfield. Wednesday, October 15, 2025, 3:30 PM. milton.

Field Hockey: Girls MS vs Winsor

Athletics: MS Category: Athletics: MS. Team: Field Hockey: MS. Opponent: Winsor. Wednesday, October 15, 2025, 3:45 PM. milton.

US 1212 Play: A Doll's House

Upper School Category: Arts. Event Type: In-person. Thursday, October 16, 2025, 7:00 PM. Studio Theater.

Football: MS Orange vs Inly

Athletics: MS Category: Athletics: MS. Team: Football: MS Orange. Opponent: Inly. Friday, October 17, 2025, 2:45 PM. milton.

Cross Country: Coed MS @ Meadowbrk

Athletics: MS Category: Athletics: MS. Team: Cross Country: MS. Opponent: Meadowbrook. Friday, October 17, 2025, 3:15 PM – 5:45 PM. Meadowbrk.

Soccer: Girls MS Orange vs BrimmerMay

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Girls Orange. Opponent: Brimmer and May. Friday, October 17, 2025, 3:15 PM. milton.

Flag Football: Boys MS vs Park

Athletics: MS Category: Athletics: MS. Team: Football: MS Blue. Opponent: Park. Friday, October 17, 2025, 3:30 PM. milton.

Soccer: Boys MS Blue vs Meadowbrk

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Boys Blue. Opponent: Meadowbrook. Friday, October 17, 2025, 3:30 PM. milton.

Soccer: Girls MS Blue vs Meadowbrk

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Girls Blue. Opponent: Meadowbrook. Friday, October 17, 2025, 3:30 PM. milton.

Volleyball: MS vs Park

Athletics: MS Category: Athletics: MS. Team: Volleyball: MS. Opponent: Park. Friday, October 17, 2025, 3:30 PM. milton.

Field Hockey: Girls MS vs BB&N

Athletics: MS Category: Athletics: MS. Team: Field Hockey: MS. Opponent: BB&N. Friday, October 17, 2025, 3:45 PM. milton.

US 1212 Play: A Doll's House

Upper School Category: Arts. Event Type: In-person. Friday, October 17, 2025, 7:00 PM. Studio Theater.

US Fall Festival

Upper School Category: Student Activities. Event Type: In-person. Friday, October 17, 2025, 8:00 PM – 10:45 PM. Quad (Rain location: Rink).

US Speech & Debate: MSDL Novice Tournament

Upper School Category: Student Activities. Event Type: In-person. Saturday, October 18, 2025. Sharon, MA.

Saturday Course Session 1: Grades 5 - 8

Employee Events Category: All Grades 6–8. All Grades K–5. Academics. Event Type: In-person. Saturday, October 18, 2025.

US 1212 Play: A Doll's House

Upper School Category: Arts. Event Type: In-person. Saturday, October 18, 2025, 7:00 PM. Studio Theater.

Blue week

Middle School Category: Academics. Event Type: In-person. Monday, October 20, 2025.

Diwali begins

Employee Events Category: Holidays. Event Type: In-person. Monday, October 20, 2025.

K-12 Diwali Celebration

Middle School Category: Academics. Event Type: In-person. Tuesday, October 21, 2025, 6:30 PM – 8:30 PM. FMC.

Football: MS Orange vs Derby

Athletics: MS Category: Athletics: MS. Team: Football: MS Orange. Opponent: Derby. Wednesday, October 22, 2025, 3:15 PM. milton.

Soccer: Boys MS Blue @ Derby

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Boys Blue. Opponent: Derby. Wednesday, October 22, 2025, 3:15 PM – 5:45 PM. Derby.

Soccer: Boys MS Orange @ Meadowbrk

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Boys Orange. Opponent: Meadowbrook. Wednesday, October 22, 2025, 3:30 PM – 5:45 PM. Meadowbrk.

Soccer: Girls MS Blue @ Rivers

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Girls Blue. Opponent: Rivers. Wednesday, October 22, 2025, 3:30 PM – 5:45 PM. Rivers.

Volleyball: MS @ Belmont DS

Athletics: MS Category: Athletics: MS. Team: Volleyball: MS. Opponent: Belmont Day. Wednesday, October 22, 2025, 3:30 PM – 5:45 PM. Belmont DS.

Birth of Bahá’u’lláh

Employee Events Category: Holidays. Event Type: In-person. Thursday, October 23, 2025.

Cross Country: Coed MS @ Park

Athletics: MS Category: Athletics: MS. Team: Cross Country: MS. Opponent: Park. Thursday, October 23, 2025, 3:30 PM – 5:45 PM. Park.

Class IV Follies

Upper School Category: Arts. Event Type: In-person. Thursday, October 23, 2025, 7:00 PM. King Theater.

Upper School Family Weekend

Upper School Category: Parents. Annual Calendar: US 2025-2026. Event Type: In-person. Friday, October 24, 2025.

US Speech & Debate: Tim Averill Invitational (Online)

Upper School Category: Student Activities. Event Type: In-person. Friday, October 24, 2025 – Saturday, October 25, 2025.

Soccer: Boys MS Blue @ Shady Hill

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Boys Blue. Opponent: Shady Hill. Friday, October 24, 2025, 3:30 PM – 5:45 PM. Shady Hill.

Soccer: Boys MS Orange @ Park

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Boys Orange. Opponent: Park. Friday, October 24, 2025, 3:30 PM – 5:45 PM. Park.

Soccer: Girls MS Orange @ Thayer

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Girls Orange. Opponent: Thayer. Friday, October 24, 2025, 3:30 PM – 5:45 PM. Thayer.

Volleyball: MS @ Shady Hill

Athletics: MS Category: Athletics: MS. Team: Volleyball: MS. Opponent: Shady Hill. Friday, October 24, 2025, 3:30 PM – 5:45 PM. Shady Hill.

Flag Football: Boys MS @ DexterSthfld

Athletics: MS Category: Athletics: MS. Team: Football: MS Blue. Opponent: Dexter/Southfield. Friday, October 24, 2025, 4:00 PM – 5:45 PM. DexterSthfld.

Football: MS Orange @ DexterSthfld

Athletics: MS Category: Athletics: MS. Team: Football: MS Orange. Opponent: Dexter/Southfield. Friday, October 24, 2025, 4:00 PM – 5:45 PM. DexterSthfld.

Class IV Follies

Upper School Category: Arts. Event Type: In-person. Friday, October 24, 2025, 7:00 PM. King Theater.

Upper School Family Weekend

Upper School Category: Parents. Annual Calendar: US 2025-2026. Event Type: In-person. Saturday, October 25, 2025.

Saturday Course Session 1: Grades 5 - 8

Employee Events Category: All Grades 6–8. All Grades K–5. Academics. Event Type: In-person. Saturday, October 25, 2025.

Middle School Professional Development Day (No Classes)

Middle School Category: Annual Calendar: MS 2025-2026. Event Type: In-person. Monday, October 27, 2025.

No classes for Upper School

Upper School Category: Annual Calendar: US 2025-2026. Event Type: In-person. Monday, October 27, 2025.

LS Family Conferences (no classes, ASP available)

Lower School Category: Annual Calendar: LS 2025-2026. Event Type: In-person. Monday, October 27, 2025.

Classes resume

Middle School Category: Academics. Annual Calendar: LS 2025-2026. Annual Calendar: MS 2025-2026. Annual Calendar: US 2025-2026. Event Type: In-person. Tuesday, October 28, 2025.

Orange week

Middle School Category: Academics. Event Type: In-person. Tuesday, October 28, 2025.

Soccer: Girls MS Blue @ DexterSthfld

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Girls Blue. Opponent: Dexter/Southfield. Wednesday, October 29, 2025.

Flag Football: Boys MS @ Derby

Athletics: MS Category: Athletics: MS. Team: Football: MS Blue. Opponent: Derby. Wednesday, October 29, 2025, 3:15 PM – 5:45 PM. Derby.

Football: MS Orange vs Beaver

Athletics: MS Category: Athletics: MS. Team: Football: MS Orange. Opponent: Beaver Country Day. Wednesday, October 29, 2025, 3:30 PM. milton.

Soccer: Boys MS Orange @ Beaver

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Boys Orange. Opponent: Beaver Country Day. Wednesday, October 29, 2025, 3:30 PM – 5:45 PM. Beaver.

Soccer: Girls MS Blue @ DexterSthfld

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Girls Blue. Opponent: Dexter/Southfield. Wednesday, October 29, 2025, 3:30 PM – 5:45 PM. DexterSthfld.

Soccer: Girls MS Orange vs Beaver

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Girls Orange. Opponent: Beaver Country Day. Wednesday, October 29, 2025, 3:30 PM. milton.

Squash: Girls MS vs DexterSthfld

Athletics: MS Category: Athletics: MS. Team: Squash: MS. Opponent: Dexter/Southfield. Wednesday, October 29, 2025, 3:30 PM. milton.

Volleyball: MS @ Meadowbrk

Athletics: MS Category: Athletics: MS. Team: Volleyball: MS. Opponent: Meadowbrook. Wednesday, October 29, 2025, 3:30 PM – 5:45 PM. Meadowbrk.

K-12 Filipinx Heritage Dinner

Lower School Category: Academics. Event Type: In-person. Thursday, October 30, 2025, 6:30 PM – 8:00 PM. Goodwin Room.

Lower School Halloween Parade

Lower School Category: All Grades K–5. Event Type: In-person. Friday, October 31, 2025.

Halloween

Employee Events Category: Holidays. Event Type: In-person. Friday, October 31, 2025.

Cross Country: Coed MS vs Thayer / BrimmerMay

Athletics: MS Category: Athletics: MS. Team: Cross Country: MS. Opponent: Thayer. Friday, October 31, 2025, 3:30 PM. milton.

Football: MS Orange @ Fessenden

Athletics: MS Category: Athletics: MS. Team: Football: MS Orange. Opponent: Fessenden. Friday, October 31, 2025, 3:30 PM – 5:45 PM. Fessenden.

Soccer: Boys MS Blue @ Fessenden

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Boys Blue. Opponent: Fessenden. Friday, October 31, 2025, 3:30 PM – 5:45 PM. Fessenden.

Soccer: Boys MS Orange vs Thayer

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Boys Orange. Opponent: Thayer. Friday, October 31, 2025, 3:30 PM. milton.

Soccer: Girls MS Blue vs Thayer

Athletics: MS Category: Athletics: MS. Team: Soccer: MS Girls Blue. Opponent: Thayer. Friday, October 31, 2025, 3:30 PM. milton.

US Speech & Debate: Xaverian Brothers Tournament

Upper School Category: Student Activities. Event Type: In-person. Saturday, November 1, 2025. Westwood, MA.

Día de Los Muertos Nov 1 - 2

Employee Events Category: Holidays. Event Type: In-person. Saturday, November 1, 2025.

MS Pike School "Fall Into Speech!" Tournament

Middle School Category: Student Activities. Event Type: In-person. Sunday, November 2, 2025. Andover, MA.

Blue week

Middle School Category: Academics. Event Type: In-person. Monday, November 3, 2025.