When Darien and New Canaan kick off at 10 a.m. on Thursday, November 26, will it be the last time the two teams meet this season? In 2021, 2023, 2024 and 2025 the answer was no. Each of those Turkey Bowls led to a playoff rematch within days. This year the game returns to DHS Stadium Field, according to the CIAC's posted Darien schedule. The quarterfinal round is set for the following Tuesday.
That puts Thanksgiving morning in the middle of a busy stretch for Darien. The week starts with a pie deadline on Heights Road. It runs through two mornings on the high school campus and could end with a second game against the same opponent. The rest of the week's calendar follows that rhythm.
A rivalry that keeps getting a second act
The series goes back to 1928, when the two teams first met on the grounds of the Ox Ridge Hunt Club. The schools have played every Thanksgiving since 1994, except in 2020, when the season was canceled. That history comes from the New Canaan football program's Turkey Bowl page, which also quotes former Darien head coach Mike Sangster: "Traditionally, in New England, Thanksgiving is football."
The winner takes home the Coaches Memorial Trophy. It honors Darien's John E. Maher, head coach from 1945 to 1965, and New Canaan's Joseph C. Sikorski, who led the Rams for 20 seasons starting in 1949.
For decades, a second meeting in the same season was rare. After a split in 1946, the teams did not meet twice in one season again until 1999. Recently it has become the usual pattern:
| Season | Turkey Bowl | Playoff rematch |
|---|---|---|
| 2021 | New Canaan 12-7 | Darien 24-10, Class LL semifinal |
| 2023 | New Canaan 31-17 | New Canaan 28-21, Class L final |
| 2024 | New Canaan 34-0 | New Canaan 35-21, Class L final |
| 2025 | New Canaan 39-7 | New Canaan 42-7, Class L quarterfinal |
The CT Insider game report covered last year's 39-7 Turkey Bowl. New Canaan now leads the all-time series 61-39-2 and the Thanksgiving series 21-9-1. The last time the game was played in Darien, in 2024, New Canaan won 34-0.
Where the standings sat going into the final stretch
Whether Thanksgiving is the first of two games depends on the Class L bracket. In the CIAC Class L rankings dated November 4, New Canaan was fifth and Darien was eighth, both inside the eight-team qualifying group. The FCIAC standings, updated through November 6 games, had New Canaan at 6-2 and Darien at 5-3. Darien's 5-3 included a 34-14 win at Ridgefield that night.
Those rankings were set before each team's last game ahead of Thanksgiving. New Canaan was scheduled to face Wilton on November 13, and Darien was scheduled to play at Stamford's Boyle Stadium at 11 a.m. on Saturday, November 14.
The playoff calendar comes right after the holiday. Per the CIAC tournament schedule:
- Quarterfinals: Tuesday, December 1
- Semifinals: Sunday, December 6
- Finals: Friday, December 11 or Saturday, December 12
The Turkey Bowl is the last regular-season game for both schools, so the CIAC rankings that set the bracket are final after Thanksgiving. Last year's rematch came in a quarterfinal held the week after the holiday. If the bracket pairs these two teams again, families who sit in the DHS stands on Thursday morning could be at another game against the same opponent five days later.
Thursday morning at DHS Stadium Field
The kickoff is set for 10 a.m. at DHS Stadium Field, according to the CIAC schedule and DAF Media's broadcast listing.
The best guide to game-day traffic is how Darien handled its last home Turkey Bowl. In 2024, Darienite published the Darien Police plan. Those rules were for 2024, so check for this year's advisory as Thanksgiving gets closer. The 2024 plan:
- All vehicles entered campus from Noroton Avenue. High School Lane and Nutmeg Lane closed to incoming traffic at 7 a.m. but stayed open to pedestrians.
- From 8:30 a.m., only cars with an event parking pass on the dashboard could enter campus.
- Drivers without a pass parked at Frate Park on Leroy Avenue, St. Thomas More Church, Middlesex School or the Noroton Heights Train Station. Shuttles ran from Middlesex School and the train station.
- Once campus parking filled, the Noroton Avenue extension closed to everything except shuttles. Rideshare drop-off and pickup happened off campus.
- Alcohol and tailgating were not allowed on school property. Bags, backpacks and coolers were subject to inspection, and bottles were not allowed.
Tickets for that 2024 game were "all but sold out" ahead of kickoff, Patch reported. When New Canaan hosted in 2025, the New Canaanite's game guide said tickets were sold in advance through GoFan, with no sales at the gate. Those are last year's rules for a different host school. Even so, waiting until Thursday morning to sort out tickets has not worked well for this game.
Friday, the high school campus gets a second morning
The Turkey Bowl is not the only event at Darien High School that holiday weekend. On Friday, November 27, the Darien Depot holds its Overstuffed Turkey Trot on the school's cross-country trail. A timed 1-mile walk or run starts at 10 a.m., and a 5K walk or run starts at 10:30 a.m. Proceeds go to The Depot, Darien's youth center. Registration is on RunSignup.
That puts big crowds on the same campus two mornings in a row, at nearly the same hour. Football on Thursday is followed by the trot on Friday, after a day of holiday cooking.
That evening, Darien Library hosts its Lit Tree Lane Stroll from 6:30 to 8 p.m. at 1441 Post Road. No registration is needed, and there is a children's craft and a scavenger hunt.
The week around the game, day by day
Here is the full stretch in order, starting the day after this post goes up:
- Friday, November 20, 5 p.m. Last call for Palmer's Market Thanksgiving orders, which include scratch-bakery pies, meals and sides. Pickup is Wednesday, November 25, at 264 Heights Road.
- Saturday, November 21. The Darien Nature Center Holiday Market runs 10 a.m. to 2 p.m. at 120 Brookside Road, with gifts from local artisans, food and face painting. From 11 a.m. to 5 p.m., the Pop Shop Holiday Market sets up at Darien Commons, outside sweetgreen at 102 Heights Road.
- Sunday, November 22, 11:30 a.m. The New Canaan Turkey Trot starts at the Waveny Park Main House, with proceeds going to Open Doors Shelter in Norwalk.
- Monday, November 23, through Thursday, December 3. The Darien Nature Center's Festival of Wreaths is open 10 a.m. to 5 p.m. at 120 Brookside Road, and every wreath on display is open for bidding.
- Wednesday, November 25. Palmer's Thanksgiving pickup.
- Thursday, November 26, 10 a.m. Darien hosts New Canaan at DHS Stadium Field.
- Friday, November 27. The Depot's Overstuffed Turkey Trot runs in the morning and the Lit Tree Lane Stroll in the evening.
- Saturday, November 28, 8 a.m. to 6 p.m. Shop Small Business Saturday, presented by the Darien Chamber, brings deals at local businesses and holiday lights on the downtown lamp posts.
- Tuesday, December 1. CIAC football quarterfinals.
- Saturday, December 5, 2 to 5 p.m. Darien's Spirit of the Season holiday event and tree lighting at Tilley Pond Park.
Darien's tree lighting falls the day before the semifinals, more than a week after Thanksgiving. The Turkey Bowl comes in the middle of that stretch, and the bracket decides whether the rivalry gets another game. The quarterfinal pairings will show whether the Blue Wave and the Rams meet again on December 1.
Our team lives the Darien and Rowayton calendar along with you, from game-day parking to the Festival of Wreaths. If this Thanksgiving week has you wondering what your own home is worth, Coastal Collective Team is happy to talk it through. Request Your Free Home Valuation.
