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.