Thanksgiving morning in Fairfield County starts with a run. On Thursday, November 26, 2026, there are 11 turkey trots in Fairfield County and nearby Milford and Orange, plus races the Sunday before and the two days after for anyone who’d rather sleep in on the holiday. Most Thanksgiving Day races start between 7:45 and 9:30 am. Most also have a kids’ fun run or a walking option, so the whole family can come.
Sunday, November 22: the early birds
Town | Race | Location |
|---|---|---|
New Canaan | New Canaan Turkey Trot | Waveny Park |
New Fairfield | Run for the Turkeys 5K Road Race | New Fairfield High School area |
Thursday, November 26: Thanksgiving Day
Town | Race | Distances | Location |
|---|---|---|---|
Bethel | Bethel Turkey Trot | See race site | Bethel Municipal Center |
Milford | Milford Turkey Trot | 3+ miles, 2 miles, 1 mile | Fowler Pavilion, behind the library |
Newtown | Newtown Turkey Trot | See race site | Newtown Middle School |
Norwalk (Rowayton) | Rowayton Turkey Trot | See race site | Rowayton Community Center |
Redding | Joyce Allen Great Turkey Escape | 5K and kids’ run | Redding Community Center |
Ridgefield | Boys & Girls Club of Ridgefield 45th Annual Turkey Trot | 5K and kids’ fun run | Boys & Girls Club of Ridgefield |
Shelton | Commodore Hull Thanksgiving Day 5K | 5K | Downtown Shelton/Derby |
Southport (Fairfield) | 49th Annual Pequot Runners Thanksgiving Day Race | 5-mile race, 2.6-mile walk | Wakeman Boys & Girls Club |
Stamford | 15th Annual Harbor Point 5K Turkey Trot & Kids’ Fun Run | 5K fun run (untimed), 8:00 am start | Harbor Point Square |
Stratford | Stratford Turkey Day Trot | See race site | Main Street |
Orange (nearby) | Rotary Club of Orange Thanksgiving Turkey Trot | 5K | Orange |
Friday and Saturday, November 27–28: the day-after crowd
Date | Town | Race | Location |
|---|---|---|---|
Fri, Nov 27 | Darien | Darien Depot Overstuffed Turkey Trot | 5K and 1-mile kids’ fun run, Darien High School cross country trail |
Fri, Nov 27 | Stamford | Shippan Turkey Trot | Near 119 Ralsey Rd and Ocean Dr East |
Sat, Nov 28 | Greenwich | 16th Annual Greenwich Alliance Turkey Trot | Mini-Trot, 1 mile and 5K, Roger Sherman Baldwin Park |
The races locals talk about
The Pequot Runners Thanksgiving Day Race in Southport is the big one on our side of the county. This is its 49th year, and for a lot of local families it’s as much a part of Thanksgiving as the turkey. Runners take on a five-mile course, and walkers have a 2.6-mile route. Register early, and plan to park on side streets near the Wakeman Boys & Girls Club.
The Harbor Point 5K in Stamford is untimed and built for fun, which makes it a good choice for first-timers and strollers. It benefits Person-to-Person, a nonprofit serving lower Fairfield County, and runners are encouraged to bring a non-perishable food item for the onsite food pantry.
The Milford Turkey Trot lets you pick your distance on race morning, from a one-mile out-and-back to a three-plus-mile loop past Gulf Beach. Ridgefield’s Boys & Girls Club trot is in its 45th year and is one of the most family-centered races in the county.
Before you lace up
Most of these races are fundraisers for a local school, club or nonprofit, and online registration usually closes a day or two before Thanksgiving. Signing up early also usually means a cheaper entry fee and a better chance at a race shirt in your size.
Plan for cold. Thanksgiving mornings along the shoreline often start in the 30s, and wind off the Sound makes the Southport, Rowayton and Shippan courses feel colder still. Wear layers you can shed, and leave a warm jacket in the car for after.
Start times and routes can change from year to year, so confirm on each race’s registration page before you go.
A few of us will be out there Thanksgiving morning too, some running and some cheering from the sidewalk with coffee in hand.
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