On a Thursday morning in late November, where do up to 4,000 runners and walkers park in Southport? That's the limit the Pequot Running Club sets for its Thanksgiving Day race and walk combined. For one morning a year, the start line takes up the streets around 385 Center Street.
The 49th Annual Pequot Runners Thanksgiving Day 5-Mile Race & 2.6-Mile Walk is on Thursday, November 26, 2026. The race and the walk both start at 8:15 a.m. from Wakeman Boys & Girls Club. The race week runs from Monday through Saturday, and it centers on two buildings. Wakeman is busy from Monday. Pequot Library is a parking lot on Thursday, gets a share of the race's giving, and opens its doors for its own event on Friday.
| Day | Where | What happens |
|---|---|---|
| Mon, Nov 23 to Wed, Nov 25 | Wakeman Boys & Girls Club | Packet pickup, 10 a.m. to 1 p.m. and 6 to 7:30 p.m. |
| Thu, Nov 26 | Wakeman, Pequot Library lot, Southport Station lots | Race-morning pickup, parking, 8:15 a.m. start |
| Fri, Nov 27 and Sat, Nov 28 | Pequot Library | Black Friday/Saturday Book Sale, 9 a.m. to 5 p.m. |
Wakeman's Thanksgiving starts on Monday
Packet pickup is what keeps Thursday morning manageable. Bibs and shirts are handed out at Wakeman Boys & Girls Club on Monday, Tuesday and Wednesday of Thanksgiving week. Each day has two windows, 10 a.m. to 1 p.m. and 6 to 7:30 p.m. The organizers ask everyone to come early in the week to avoid long lines on race morning. You can also collect packets for family members or friends if they know you're picking up for them. The race site has a Find a Participant tool for checking registrations before you go.
There's also a Thursday morning pickup, but the race's own pages list different times for it. The main race page on RunSignup says 7 to 8 a.m. The race FAQ gives 6:30 to 7:30 a.m., and the Pequot Running Club's race page also has pickup starting at 6:30. If your plan depends on getting a bib that morning, check with the organizers first. A Monday evening stop at Wakeman avoids the question entirely.
Registration is still open. Adults pay $43.23 for either the race or the walk, processing fee included. Ages 1 to 17 pay $37.90 for the race and $31.49 for the walk. There's no separate children's race on the registration page, so younger family members do one of the two main events.
Thursday's parking puts the race in the library lot
The 2026 race page lists the parking. Use the Southport Train Station East and West lots, Pequot Library, Southport Congregational Church, and designated retail lots along Post Road. The organizers also say the roads around Wakeman close ahead of the 8:15 start, so arrive early.
That makes Pequot Library a staging area on Thursday morning, even for neighbors who aren't running. It's also why the start-time change matters. The Town of Westport's 2025 advisory listed an 8 a.m. start last year. The 2026 start is 8:15, "sharp," for both events.
The two events have different rules for who comes along:
- Strollers and baby joggers are allowed only in the 2.6-mile walk.
- Dogs may join the walk on a short leash. No pets are allowed in the 5-mile race.
- Wheeled devices of any kind are prohibited in the race.
The 5 miles leave Fairfield before they come back
The 5-mile course spends much of its distance in Westport. Here is the route the Town of Westport published for the 2025 race, as Patch reported in its traffic advisory. Runners left Southport and:
- Entered Westport from Pequot Avenue and Beachside Avenue
- Ran north on Sasco Creek Road
- Turned east on Greens Farms Road
- Went northwest on Clapboard Hill Road
- Headed south on Maple Avenue South
- Turned west again on Greens Farms Road
- Ran south on New Creek Road
- Went east on Beachside Avenue, back into Southport on Pequot Avenue
That's last year's route. The 2026 race materials say local roads will close but don't yet list the streets. Last year, the Town of Westport warned of temporary closures and delays and expected the race to clear Westport roads by about 11 a.m. If you're hosting on Greens Farms Road or Beachside Avenue, plan for that kind of morning until this year's advisory comes out.
The front of the field moves quickly. Club records are James Maniscalo's 24:09 from 2021 and Allie Ostrander's 27:13 from 2022. In 2024, the club started a Seeded Runner Program for men under 27 minutes and women under 34 minutes. Seeded runners get a dedicated room for stretching and leaving gear, plus an escorted walk to a corral at the front of the start. At the finish, the approach is coned into two lanes, men on the left and women on the right, until 30 of each have crossed. The top 30 in each group get a card they can trade for an elite finisher shirt in their own size at the awards tent. After that, the full width of the road opens to everyone.
Where the entry fees go
The Pequot Running Club says the race started in 1978 as a small club run. The race page now describes a Southport holiday tradition that "brings thousands of runners, walkers, families, and neighbors together." It names the Wakeman Boys & Girls Club, Caroline House, Junior Achievement, Pequot Library and Westport EMS among the organizations it supports.
The race's donation page lists 15 organizations as last year's grant recipients, including the Burroughs Community Center. It also says 100% of donations go to the recipients. The two buildings at the center of the week are both on that list. Wakeman hosts the start and receives a grant. Pequot Library provides parking on Thursday and also receives a grant. On Friday, the library starts raising money of its own.
After the race, the club promises refreshments, music, and awards for overall and age-group winners. There's also a prize raffle. The 2026 race page says everyone who registers before race day is entered, you don't have to be present to win, and the winners list is posted before the race on Thursday morning. Prizes are picked up after the race at the Pequot tent on the turf field, or in the Warren gym if the weather is bad.
Friday, the same lot fills again
The day after Thanksgiving, Pequot Library holds its Black Friday/Saturday Book Sale on November 27 and 28, 9 a.m. to 5 p.m. both days. Admission is free and items are priced as marked. The library describes more than 10,000 books and media items in like-new or gently used condition. They include art and photography, children's books, holiday titles, cookbooks and fiction, with CDs and DVDs at $1 to $3 each.
The library calls it a holiday-shopping sale. It's one of several seasonal sales on the library's calendar, along with the Summer, Midwinter and Spring Blowout sales. Proceeds support library services, programs and events, Special Collections exhibitions and school outreach. So in one weekend, the library gets money twice: once through the race's grants and again through its own sale.
The November dates on either side
Thanksgiving week is the busiest stretch, but other Fairfield dates fall before and after it.
Saturday, November 14. The Fairfield Museum hosts Meet Santa at the Holiday Pop-Up Market at 370 Beach Road from 10 a.m. to 12:30 p.m. Visiting Santa is free for children 12 and under. Adult market admission is $5 at the door, cash or card, and proceeds support the museum's education programs and free community events.
Friday, November 20. The Friends of the Library hold their Big Fall Book Sale in the Rotary Room at the Fairfield Public Library's Main Library, 9 a.m. to 4:30 p.m. Books and DVDs cost $1 to $5, with some special items priced higher. That's one week before the Pequot Library sale, which puts two Fairfield library book sales seven days apart.
Thursday, December 10. The Holiday Shop & Stroll runs from 6 to 9 p.m., with special discounts at participating stores and other events around town. A pre-event happy hour runs from 5 to 6 p.m. at the Fairfield University Store, Second Story. The organizers say it's rain or shine.
Between November 23 and 28, Wakeman hands out bibs for three days and hosts the start, and Pequot Library's lot serves a 5-mile race on Thursday and a 10,000-item book sale on Friday.
If your house is on or near the Southport course and you've wondered what it's worth before next year's race, M & D Properties would be glad to walk you through it. Request a Home Valuation, and we'll put together a careful number for your Fairfield home.