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October 2026
Sunday Monday Tuesday Wednesday Thursday Friday Saturday
Sunday, September 27
Monday, September 28
Calleva Trip - Class of 2030
All Day
Calleva Trip - Class of 2030
All Day
Odd/Arts A
All Day
Odd/Arts A
All Day
Middle School Golf vs. St. Francis Xavier School (Home)
Whiskey Creek Country Club
Athletics Golf - Middle School Co-Ed - Game St. Francis Xavier School - Home
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Whiskey Creek Country Club
All School 2026-2027 Mahj Mondays
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Ellenberg Library, Middle School Patio
Tuesday, September 29
Calleva Trip - Class of 2030
All Day
Even/Arts B
All Day
Even/Arts B
All Day
Lower School 2026-2027 Registration for Lower School Clubs
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https://www.canterburyfortmyers.org/lower-school-clubs
Middle School Volleyball White vs. First Baptist Academy (Home)
Canterbury School - O-Gym
Athletics Volleyball - Middle School Girls White - Game First Baptist Academy - Home
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Canterbury School - O-Gym
Middle School Volleyball Blue vs. First Baptist Academy (Home)
Canterbury School - O-Gym
Athletics Volleyball - Middle School Girls Blue - Game First Baptist Academy - Home
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Canterbury School - O-Gym
Middle School Football vs. Community School of Naples (Away)
Community School of Naples
Varsity Swimming vs. Dunbar High School (Away)
STARS Complex
Athletics Swimming - Varsity Co-Ed - Game Dunbar High School - Away
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STARS Complex
Athletics Football - Middle School - Game Community School of Naples - Away
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Community School of Naples
Wednesday, September 30
Calleva Trip - Class of 2030
All Day
Senior Portraits Roadshow
All Day
Upper School Art Room
Senior Portraits Roadshow
All Day
Upper School Art Room
Odd/Arts A
All Day
Odd/Arts A
All Day
Middle School Golf vs. Community School of Naples (Home)
Whiskey Creek Country Club
Athletics Golf - Middle School Co-Ed - Game Community School of Naples - Home
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Whiskey Creek Country Club
Thursday, October 1
Calleva Trip - Class of 2030
All Day
Even/Arts B
All Day
Even/Arts B
All Day
Middle School Volleyball White vs. Seacrest School (Away)
Seacrest School
Athletics Volleyball - Middle School Girls White - Game Seacrest School - Away
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Middle School Volleyball Blue vs. Seacrest School (Away)
Seacrest School
Varsity Boys Golf vs. Aubrey Rogers CANCELLED (Home)
Cypress Lake Country Club
Athletics CANCELLED - Golf - Varsity Boys - Game Aubrey Rogers - Home
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Cypress Lake Country Club
Athletics Volleyball - Middle School Girls Blue - Game Seacrest School - Away
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Junior Varsity Volleyball vs. Aubrey Rogers (Home)
Canterbury School - Murphy Sports Center
Athletics Volleyball - Junior Varsity Girls - Game Aubrey Rogers - Home
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Canterbury School - Murphy Sports Center
Varsity Volleyball vs. Aubrey Rogers (Home)
Canterbury School - Murphy Sports Center
Varsity Swimming (Away)
North Fort Myers High School
Athletics Volleyball - Varsity Girls - Game Aubrey Rogers - Home
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Canterbury School - Murphy Sports Center
Athletics Swimming - Varsity Co-Ed - Game - Away
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North Fort Myers High School
Friday, October 2
Calleva Trip - Class of 2030
All Day
SWFTS Upper School Thespian Competition
All Day
Off Campus
SWFTS Upper School Thespian Competition
All Day
Off Campus
Cross-Country - Varsity Co-Ed - Game - Away
All Day
Cross-Country - Varsity Co-Ed - Game - Away
All Day
Odd/Arts A
All Day
Odd/Arts A
All Day
Varsity Cross Country (Away)
Middle School Golf vs. Southwest Florida Christian Academy (Home)
Whiskey Creek Country Club
Athletics Golf - Middle School Co-Ed - Game Southwest Florida Christian Academy - Home
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Whiskey Creek Country Club
Middle School Volleyball White vs. Community School of Naples (Home)
Canterbury School - O-Gym
Athletics Volleyball - Middle School Girls White - Game Community School of Naples - Home
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Canterbury School - O-Gym
Athletics Cross-Country - Middle School Co-Ed - Game - Away
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Holloway Park
Middle School Volleyball Blue vs. Community School of Naples (Home)
Canterbury School - O-Gym
Athletics Volleyball - Middle School Girls Blue - Game Community School of Naples - Home
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Canterbury School - O-Gym
Varsity Football vs. St. Stephen's Episcopal School (Away)
St. Stephen's Episcopal School
Athletics Football - Varsity - Game St. Stephen's Episcopal School - Away
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St. Stephen's Episcopal School
Saturday, October 3
Calleva Trip - Class of 2030
All Day
SWFTS Upper School Thespian Competition
All Day
Off Campus
Cross-Country - Varsity Co-Ed - Game - Away
All Day
Cross-Country - Varsity Co-Ed - Game - Away
All Day
Varsity Cross Country (Away)
Varsity Volleyball vs. Bonita Springs High School (Away)
Estero Recreation Center
Athletics Volleyball - Varsity Girls - Game Bonita Springs High School - Away
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Estero Recreation Center
Varsity Volleyball vs. Gulf Coast High School (Away)
Estero Recreation Center
Athletics Volleyball - Varsity Girls - Game Gulf Coast High School - Away
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Estero Recreation Center
Varsity Volleyball vs. Charlotte High School (Away)
Estero Recreation Center
Athletics Volleyball - Varsity Girls - Game Charlotte High School - Away
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Estero Recreation Center
Varsity Boys Golf vs. The Village School (Away)
Bonita Bay East
Athletics Golf - Varsity Boys - Game The Village School - Away
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Bonita Bay East
Sunday, October 4
Monday, October 5
Even/Arts B
All Day
Even/Arts B
All Day
Tuesday, October 6
Odd/Arts A
All Day
Odd/Arts A
All Day
Varsity Boys Golf (Away)
Valencia Golf & Country Club
Varsity Girls Golf (Away)
Valencia Golf & Country Club
Athletics Golf - Varsity Boys - Game - Away
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Valencia Golf & Country Club
Athletics Golf - Varsity Girls - Game - Away
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Valencia Golf & Country Club
Middle School Volleyball Blue vs. Evangelical Christian School (Home)
Canterbury School - Murphy Sports Center
Junior Varsity Volleyball vs. Seacrest School (Away)
Seacrest School
Athletics Volleyball - Junior Varsity Girls - Game Seacrest School - Away
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Seacrest School
Athletics Volleyball - Middle School Girls Blue - Game Evangelical Christian School - Home
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Canterbury School - Murphy Sports Center
Varsity Volleyball vs. Seacrest School (Away)
Seacrest School
Athletics Volleyball - Varsity Girls - Game Seacrest School - Away
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Seacrest School
Wednesday, October 7
Even/Arts B
All Day
Even/Arts B
All Day
BLOOD DRIVE - US PARKING LOT - 7:30 AM TO 2:00 PM
All Day
BLOOD DRIVE - US PARKING LOT - 7:30 AM TO 2:00 PM
All Day
Upper School 2026-2027 National Merit Scholarship Qualifying Test (NMSQT) Grades 10 & 11
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Ellenberg Library, Frank L. Romano Performing Arts Center
Middle School Football vs. Out of Door Academy (Home)
Canterbury School - FineMark Field
Athletics Football - Middle School - Game Out of Door Academy - Home
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Thursday, October 8
Odd/Arts A
All Day
Odd/Arts A
All Day
Cougar Growl
All Day
Murphy Sports Center
Cougar Growl
All Day
Murphy Sports Center
Varsity Girls Golf vs. Oasis High School (Home)
Heritage Palms Golf and Country Club
Athletics Golf - Varsity Girls - Game Oasis High School - Home
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Heritage Palms Golf and Country Club
Middle School Golf vs. Evangelical Christian School (Away)
Hideaway Country Club
Athletics Golf - Middle School Co-Ed - Game Evangelical Christian School - Away
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Hideaway Country Club
All School 2026-2027 Fathers Club Happy Hour
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Vybe - Bell Tower
Friday, October 9
Even/Arts B
All Day
Even/Arts B
All Day
All School 2026-2027 Founders' Day
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Murphy Sports Center & Hilliard Library
All School 2026-2027 Homecoming Alumni Event
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Middle School Patio
Varsity Football vs. Santa Fe Catholic High School (Home)
Canterbury School - FineMark Field
Athletics Football - Varsity - Game Santa Fe Catholic High School - Home
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Canterbury School - FineMark Field
Saturday, October 10
Seniors Last Day to be Photographed
All Day
Seniors Last Day to be Photographed
All Day
Cross-Country - Varsity Co-Ed - Game - Away
All Day
Cross-Country - Varsity Co-Ed - Game - Away
All Day
Varsity Cross Country (Away)
Upper School 2026-2027 Homecoming Dance
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Sunday, October 11
Accreditation Visit
All Day
Accreditation Visit
All Day
Monday, October 12
Accreditation Visit
All Day
Odd/Arts A
All Day
Odd/Arts A
All Day
Tuesday, October 13
Accreditation Visit
All Day
Even/Arts B
All Day
Even/Arts B
All Day
Middle School Football vs. Evangelical Christian School (Home)
Canterbury School - FineMark Field
Varsity Swimming vs. Community School of Naples (Away)
Norris Aquatic Center
Varsity Volleyball vs. Evangelical Christian School (Home)
MSC - MSC Gym - 508
Athletics Football - Middle School - Game Evangelical Christian School - Home
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Canterbury School - FineMark Field
Athletics Volleyball - Varsity Girls - Game Evangelical Christian School - Home
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MSC MSC Gym
Athletics Swimming - Varsity Co-Ed - Game Community School of Naples - Away
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Wednesday, October 14
Odd/Arts A
All Day
Odd/Arts A
All Day
Middle School 2026-2027 Eighth Grade Washington, D.C. Trip Meeting
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Ellenberg Library
Thursday, October 15
Even/Arts B
All Day
Even/Arts B
All Day
School Picture Retakes/Makeup
All Day
Upper School Art Room
School Picture Retakes/Makeup
All Day
Upper School Art Room
Middle School Golf (Away)
Bonita Bay East
Athletics Golf - Middle School Co-Ed - Game - Away
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Bonita Bay East
Varsity Boys Golf vs. Fort Myers High School (Home)
Cypress Lake Country Club
Varsity Girls Golf vs. Bishop Verot High School (Home)
Heritage Palms Golf and Country Club
Athletics Golf - Varsity Boys - Game Fort Myers High School - Home
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Cypress Lake Country Club
Athletics Golf - Varsity Girls - Game Bishop Verot High School - Home
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Heritage Palms Golf and Country Club
Varsity Swimming vs. Bishop Verot High School (Away)
Fort Myers Aquatic Center
Athletics Swimming - Varsity Co-Ed - Game Bishop Verot High School - Away
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Fort Myers Aquatic Center
Varsity Volleyball vs. Out of Door Academy (Home)
MSC - MSC Gym - 508
Athletics Volleyball - Varsity Girls - Game Out of Door Academy - Home
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MSC MSC Gym
Friday, October 16
Conferences - No Classes
All Day
Conferences - No Classes
All Day
Cross-Country - Varsity Co-Ed - Game - Away
All Day
Cross-Country - Varsity Co-Ed - Game - Away
All Day
Varsity Cross Country (Away)
Varsity Football vs. Gateway Charter School CANCELLED (Home)
Canterbury School - FineMark Field
Athletics CANCELLED - Football - Varsity - Game Gateway Charter School - Home
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Canterbury School - FineMark Field
Saturday, October 17
Sunday, October 18
Monday, October 19
Conferences - No Classes
All Day
Conferences - No Classes
All Day
Upper School 2026-2027 School Day SAT for Juniors
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Ellenberg Library
Tuesday, October 20
Odd/Arts A
All Day
Odd/Arts A
All Day
Varsity Boys Golf vs. Oasis High School (Away)
Cape Royal Golf Club
Varsity Girls Golf vs. Bishop Verot High School (Away)
Myerlee Country Club
Athletics Golf - Varsity Boys - Game Oasis High School - Away
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Cape Royal Golf Club
Athletics Golf - Varsity Girls - Game Bishop Verot High School - Away
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Myerlee Country Club
Varsity Volleyball (TBD)
Middle School Football (Away)
First Baptist Academy
Athletics Football - Middle School - Game - Away
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First Baptist Academy
Athletics Volleyball - Varsity Girls - Game - TBD
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Wednesday, October 21
Even/Arts B
All Day
Even/Arts B
All Day
Arts Performances 2026-2027 Little Women
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Frank L. Romano Performing Arts Center
Thursday, October 22
Odd/Arts A
All Day
Odd/Arts A
All Day
Varsity Boys Golf vs. Estero High School (Away)
Pelican Sound
Athletics Golf - Varsity Boys - Game Estero High School - Away
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Pelican Sound
Arts Performances 2026-2027 Little Women
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Frank L. Romano Performing Arts Center
Friday, October 23
Even/Arts B
All Day
Even/Arts B
All Day
Arts Performances 2026-2027 Little Women
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Frank L. Romano Performing Arts Center
Varsity Football vs. Out of Door Academy (Away)
Out-of-Door Academy
Athletics Football - Varsity - Game Out of Door Academy - Away
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Out-of-Door Academy
Saturday, October 24
Volleyball - Varsity Girls - Game - TBD
All Day
Volleyball - Varsity Girls - Game - TBD
All Day
Varsity Volleyball (TBD)
All School 2026-2027 Carnival
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Mason Goss '86 Field and Upper School Rubenstein Courtyard
Sunday, October 25
Monday, October 26
Wax Museum Setup
All Day
Wax Museum Setup
All Day
Odd/Arts A
All Day
Odd/Arts A
All Day
Tuesday, October 27
Even/Arts B
All Day
Even/Arts B
All Day
Third Grade Wax Museum
All Day
Frank L. Romano Performing Arts Center
Third Grade Wax Museum
All Day
Frank L. Romano Performing Arts Center
Upper School 2026-2027 School Day ACT
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Ellenberg Library
Varsity Boys Golf (Away)
Valencia Golf & Country Club
Varsity Girls Golf (Away)
Valencia Golf & Country Club
Athletics Golf - Varsity Girls - Game - Away
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Valencia Golf & Country Club
Athletics Golf - Varsity Boys - Game - Away
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Valencia Golf & Country Club
Varsity Swimming (TBD)
Community School of Naples
Athletics Swimming - Varsity Co-Ed - Game - Neutral
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Community School of Naples
Varsity Boys Soccer vs. Naples High School (Away)
Naples High School
Athletics Soccer - Varsity Boys - Game Naples High School - Away
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Naples High School
Wednesday, October 28
Odd/Arts A
All Day
Odd/Arts A
All Day
Varsity Girls Soccer vs. North Fort Myers High School (Home)
Canterbury School - FineMark Field
Athletics Soccer - Varsity Girls - Game North Fort Myers High School - Home
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Canterbury School - FineMark Field
Thursday, October 29
Even/Arts B
All Day
Even/Arts B
All Day
Varsity Boys Soccer vs. Lely High School (Away)
Lely High School
Athletics Soccer - Varsity Boys - Game Lely High School - Away
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Lely High School
Friday, October 30
Odd/Arts A
All Day
Odd/Arts A
All Day
All School 2026-2027 Mothers & Fathers Club Coffee: Trunk or Treat!
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Middle School Patio
Lower School 2026-2027 Halloween Parade and Trunk-or-Treat
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Finemark Field, Middle School Parking Lot
Varsity Football vs. Marco Island Academy (Away)
Marco Island Academy
Athletics Football - Varsity - Game Marco Island Academy - Away
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Marco Island Academy
Saturday, October 31