August 2026
- Monday, August 31 – New Family Orientation
September 2026
- Tuesday, September 1 – First Day of School (8:15am Welcome Back Coffee under Pavilion)
- Monday, September 7 – No School: Labor Day
- Monday, September 21 – No School: Yom Kippur
- Wednesday, September 23 – Back to School Night
- Saturday, September 26 – Welcome Back Party
- Wednesday, September 30 – Picture Day
October 2026
- Friday, October 2 – Friday Night Lights at Dedham Country Day School
- Monday, October 12 – No School: Indigenous Peoples’ Day
- Thursday, October 15 – New Parent & Caregiver Dinner
- Wednesday, October 21 – No School: Parent/Teacher Conference Day (EDP Available/No Bus)
- Friday, October 23 – 8:30am Sharing Assembly
- Saturday, October 24 – CRS Fair
- Friday, October 30 – No School: Parent/Teacher Conference Day (EDP Available/No Bus)
November 2026
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Tuesday, November 10 – No Athletics Extended Faculty Meeting (EDP Available/No Study Hall/Bus Leaves at 4:30pm)
- Friday, November 13 – 8:30am Sharing Assembly
- Monday, November 23 – Friday, November 27 – School Not In Session: Fall Break
December 2026
- Friday, December 18 – Noon Dismissal / Winter Festival (No EDP/Bus Leaves at 12:00pm)
- Monday, December 21 – Friday, January 1 – School Not In Session: Winter Break
January 2027
- Monday, January 4 – School Reconvenes
- Friday, January 15 – No School: Professional Development (EDP Available/No Bus)
- Monday, January 18 – No School: Martin Luther King Day
February 2027
- Wednesday, February 3 – State of the School and Look Ahead; 6:30pm Zoom Option
- Friday, February 5 – 8:30am Sharing Assembly
- Monday, February 15 – No School: Presidents’ Day
- Tuesday, February 16 – No School: Parent/Teacher Conference Day (EDP Available/No Bus)
- Thursday, February 25 – No School: Parent/Teacher Conference Day (EDP Available/No Bus)
- Friday, February 26 – 8:30am Sharing Assembly
March 2027
- Monday, March 15 – Friday, March 26 – School Not in Session Spring Break
- Monday, March 29 – School Reconvenes
April 2027
- Monday, April 19 – No School: Patriots’ Day
- Friday, April 23 – 8:30am Sharing Assembly
May 2027
- Friday, May 7 – Noon Dismissal / May Day (No EDP/Bus Leaves at 12:00pm)
- Friday, May 28 – Noon Dismissal / Sports Day (EDP Available/Bus Leaves at 4:30pm)
- Monday, May 31 – No School: Memorial Day
June 2027
- Friday, June 4 – 8:30am Sharing Assembly
- Wednesday, June 9 – Last Day of School / Grade 8 Graduation 5:00 pm (No EDP/ Bus Leaves at 12:00pm)