This year, Fairfield County's Thanksgiving races start on Sunday, Nov. 22, and the last one runs on Saturday, Nov. 28. Between those days there are races on Thanksgiving morning in at least eight towns, a Friday race in Darien and a Saturday race in Greenwich. The Stamford parade lands on the first Sunday, close to the start of two other races.
So the real question is which day of the week fits how your family spends the holiday. Some of the dates that decide what you pay arrive before Thanksgiving week does.
The First Deadline Lands Nov. 1
Most of these race pages raise prices on a schedule, and several of the increases come before Thanksgiving. Here they are in date order:
- Nov. 1. The Greenwich Alliance Turkey Trot adult entry goes from $40 to $50 and reaches $55 on race day. The Darien Depot Overstuffed Turkey Trot adult entry is $45 through Nov. 1, then $50 from Nov. 2 to 26 and $55 on race day, plus fees.
- Nov. 8. The Stratford Turkey Day Trot stops guaranteeing shirt sizes for its long-sleeve shirt. Organizers say they order shirts on Nov. 9 and may have none left over after that.
- Nov. 20. Stratford's price goes up after 11:59 p.m. The New Canaan Turkey Trot also opens early check-in that day at the New Canaan Library, 3 to 5 p.m.
- Nov. 21. New Canaan's second early check-in runs 10 a.m. to 1 p.m. at the library. Stamford's balloon inflation party is that afternoon.
Stratford is the one race here with a published cap. It allows 1,000 runners, and in late October its page showed 726 spots left. Waiting until the night before is a gamble at most of these races, and at Stratford it's a real one.
Sunday, Nov. 22 Asks You to Pick One
The Sunday before Thanksgiving is the most crowded morning of the week, and its three main events start within an hour of each other.
The New Fairfield Run for the Turkeys starts at 11 a.m. from 54 Gillotti Road, and entry is listed at $27.50 including the fee. The New Canaan Turkey Trot starts at 11:30 a.m. at the Waveny Park Main House. The 5K was listed at $44.30 including the fee, with a children's rate for ages 12 and under. This year's listing says "Back to the original course." The race calls itself a short run through Waveny "the Sunday before the holiday," with race-day check-in from 10:30 a.m.
At noon, Stamford starts the 33rd Stamford Downtown Parade Spectacular, which runs until 2 p.m. CT Insider reports the parade will have 15 giant balloons, including Clifford the Big Red Dog, Peppa Pig, Rudolph and Bumble the Abominable Snowman. The route starts at Summer and Hoyt streets and ends at Atlantic and Federal. The Stamford Downtown Special Services District says the parade draws about 100,000 spectators a year. The same report names two groups joining the parade for the first time this year: the Pajaro Campana Center for Dance and Culture and the Zappy Zebra's Parade Team. They march with the University of New Haven Marching Band, the NYPD Emerald Society Pipe & Drum Band, Fairfield County Pipes & Drums and high school bands from Westhill, Brentwood, Port Chester, Uniondale and Wyandanch.
A 5K that starts at Waveny at 11:30 and a parade that steps off downtown at noon can't share a morning. If your household wants both, the parade has a second chance built in. The Point72 Giant Balloon Inflation Party runs Saturday, Nov. 21, from 3 to 6 p.m. at Hoyt and Summer. CT Insider reports Point72 has hosted it since 2014. Families can see the balloons up close on Saturday and keep Sunday morning for Waveny.
Thanksgiving Morning Runs on a Staggered Clock
On Thursday, Nov. 26, the start times are spread from 7:45 to 9 a.m. That spread decides what you can fit around the turkey and the guests better than distance from home does.
| Race | Start | Where | Distances | Listed adult entry |
|---|---|---|---|---|
| Newtown Turkey Trot | 7:45 a.m. | Newtown Middle School, 11 Queen St. | 5K run, 2.5K walk | $38.10 incl. fee |
| Bethel Turkey Trot | 8 a.m. | Bethel Municipal Center, 1 School St. | 5K | $38.10 incl. fee |
| Harbor Point 5K Turkey Trot | 8 a.m. | Harbor Point Square, Stamford | 5K, untimed | Free, RSVP required |
| Commodore Hull Thanksgiving Day 5K | 8 a.m. | 44 Canal St., Shelton | 5K | $35 |
| Pequot Runners Thanksgiving Day Race | 8:15 a.m. | Wakeman Boys & Girls Club, Southport | 5 miles, 2.6-mile walk | $43.23 incl. fee |
| Stratford Turkey Day Trot | 8:15 a.m. | Main St. in front of the theatre | 5K | $44.46 incl. fee |
| Ridgefield Turkey Trot | 8:30 a.m. | Boys & Girls Club, 41 Governor St. | 5K, kids' fun run | $38.96 incl. fee |
| Rowayton Turkey Trot | 9 a.m. | Rowayton Community Center | 5K, kids' 1 mile | Online registration |
All prices are as listed in late October.
The races also differ in what they ask of a family. The Pequot Runners race is five miles, longer than every other race on the table, and has used seeded entry since 2024. Its 2.6-mile walk is the shorter option for relatives who aren't racing. The Harbor Point 5K, now in its 15th year, is free and untimed. Check-in opens at 7:30 a.m. Adults need an RSVP and an online waiver, and walk-ups are allowed.
Stratford's listing this year includes a new course map. The race is in its 24th year and starts and finishes on Main Street by the theatre. The listing describes a route along East Broadway and Elm Street, then a loop by the park. A free kids' run for ages 9 and under goes off at 8:05 a.m., and bib pickup that morning runs from 7 to 8:10 a.m.
Shelton's Commodore Hull 5K is in its 25th year. It starts in downtown Shelton and runs through Derby. Entry is free for runners ages 70 to 99, and youth entry is $25. Proceeds go to the Boys & Girls Club of the Lower Naugatuck Valley.
Every one of these races also raises money for something local. Newtown's benefits C.H. Booth Library. Bethel's supports Ability Beyond and Bethel Parks & Recreation. Ridgefield's is the 45th annual race presented by the Boys & Girls Club of Ridgefield. Rowayton's adds the Gobble Gallop, a one-mile kids' run.
Friday and Saturday Are for the Guests Who Stayed
Two races are set for after the holiday, when out-of-town family is still around and Thursday's schedule has passed.
On Friday, Nov. 27, the Darien Depot Overstuffed Turkey Trot holds a timed one-mile walk/run at 10 a.m. and a 5K walk/run at 10:30 a.m., both on the Darien High School cross-country trail. Proceeds go to The Depot, Darien's youth center. Ages 6 to 12 pay $30 plus fees, and children 5 and under run free. The race lists Nov. 28 as its snow date. Because it's on trail, not pavement, this race works differently from the rest of the week's 5Ks.
On Saturday, Nov. 28, the Greenwich Alliance holds its 16th annual Turkey Trot from Roger Sherman Baldwin Park at 100 Arch Street, on a flat loop through Bruce Park. Greenwich Road Runners direct the race. It's the largest fundraiser for the Greenwich Alliance for Education, which marks 20 years in 2026. The Mini-Trot for ages 3 to 5 starts at 9 a.m., the one-mile fun run/walk at 9:30 and the certified 5K at 10. Anyone away that weekend can do a $25 virtual 5K, logging their time starting Nov. 28.
Matching the Day to the Holiday
Once the whole week is laid out, choosing a race comes down to the household's Thanksgiving schedule:
- Hosting dinner Thursday? The Sunday races at Waveny and New Fairfield, or the Saturday loop through Bruce Park, keep Thanksgiving morning free for the kitchen.
- Small children in the group? Stratford's free kids' run, Rowayton's Gobble Gallop, Ridgefield's 8 a.m. kids' fun run and Greenwich's Saturday Mini-Trot are the shortest races on the week's schedule.
- Mixed ages and paces? Harbor Point is free and untimed, and Pequot pairs its five-miler with a 2.6-mile walk.
- Guests arriving Wednesday night? Rowayton at 9 a.m. is the latest Thursday start on the table, and Darien's Friday race gives a houseful of visitors a fresh reason to get outside.
The week after brings the December strolls. Ridgefield's Holiday Stroll is Friday, Dec. 4, presented by the Ridgefield Chamber of Commerce. Rowayton's two-day stroll on Dec. 4 and 5 adds a full-day expanded holiday market and its second annual Holiday Bike Parade. Westport's downtown stroll runs Dec. 5 from 4 to 7 p.m. Darien's free An Old Fashion Holiday at Tilley Pond Park runs Dec. 5 from 2 to 5 p.m. On Dec. 6, Stamford's Heights & Lights brings the Santa rappel, fireworks and tree lighting to Latham Park. Stamford Downtown advises skipping the Bedford Street Garage because of ongoing construction.
When relatives come for the holiday, the conversation after the race often turns to what homes near Waveny, Bruce Park or the Southport start line sell for. I'm glad to walk you through those numbers whenever you'd like. Brenda Colon can help. Book a complimentary market consultation.
