Fairfield's Holiday Season Runs Through One Building on Beach Road
November 5, 2026
November 5, 2026
Tomorrow at 4 p.m., the Fairfield Museum and History Center at 370 Beach Road opens its doors to holiday shoppers, with local makers selling handmade goods and a wine and cheese reception. In two weeks, after the town's tree and menorah lighting, the same building opens again for a model train show. The museum's calendar has the season's opening date and the Saturday of Thanksgiving weekend, and almost everything else on Fairfield's holiday calendar this year happens between those two nights.
This is the 12th annual Holiday Pop-Up Market. It runs Friday, November 13, from 4 to 7 p.m., with a wine and cheese reception, and Saturday, November 14, from 10 a.m. to 4 p.m. Santa visits on Saturday from 10 a.m. to 12:30 p.m., so families with young children should plan for the morning.
Admission is a $5 donation, cash or card at the door. Each donation enters you in a drawing for a family museum membership and a gift bag of favorites from the Museum Shop. The museum says all proceeds support its educational programs and free community events. That last detail matters later in the season.
The museum describes this year's market as having "a record number of new vendors alongside longtime favorites," and every vendor space is sold out. The published lineup covers the usual gift categories, and most of the names are small studios and makers:
Our Woven Community is a program of the Burroughs Community Center, so a purchase there also supports a nearby nonprofit.
The other new addition is outside. The Inclusive Brew will be parked outside the museum on Saturday, serving coffee and seasonal drinks, and you don't need a ticket to buy a cup. That means someone can grab a coffee while the rest of the group shops, or stop by on a Saturday walk without going in.
One more note from the museum. It has seen fake social media posts recruiting vendors and asking for entry fees for this market. The museum says it collects fees only through fairfieldhistory.org, by physical check in person, or by credit card over the phone, and that official messages come only from staff email addresses ending in @fairfieldhs.org. If you see a suspicious post, the museum asks you to call 203-259-1598. Since every vendor space is already sold out, any post still selling a booth is a red flag.
The museum doesn't go quiet after the market. On Tuesday, November 17, from 6 to 7 p.m., it co-presents a free talk called "Buildings that Remember" with the Fairfield Public Library, held at the library at 1080 Old Post Road. It's part of the museum's Local to Fairfield series, and it's one of the free community events that the market's $5 donations help pay for.
If your mid-November routine includes coffee and a pastry on Post Road, there's a new option. Kneads, a bakery-café that already has a Westport location, opened at 1916 Post Road the week of October 14, according to Patch. Patch reported that Kneads makes its breads and pastries from scratch with grain from regional producers and stone-mills organic whole grains. It serves coffee, breakfast and lunch.
Thanksgiving weekend starts in Southport and ends back at the museum.
| Day | Event | Where | Time | Cost |
|---|---|---|---|---|
| Thursday, Nov. 26 | 49th annual Pequot Runners Thanksgiving Day race: 5 miles, plus a 2.6-mile walk | Starts at Wakeman Boys & Girls Club, 385 Center Street, Southport | 8:15 a.m. | Registration through the race page |
| Saturday, Nov. 28 | Town tree and menorah lighting, then the Holiday Express Train Show grand opening | Train show at the Fairfield Museum, 370 Beach Road | Train show 5 to 7 p.m. | $3 per person, $10 for a family of four |
| Sunday, Nov. 29 | Santa's Arrival Fairfield 2026 | Sherman Green, corner of Post Road and Reef Road | 10 a.m. to 2 p.m. | Free |
The Pequot Runners race starts in Southport early enough to finish before the cooking starts. This year is its 49th.
The museum's listing for Saturday night describes the order of events: "Warm up at the Fairfield Museum after the town's tree and menorah lighting ceremony and be one of the first to see the cozy displays of the Holiday Express Train Show!" The grand opening runs from 5 to 7 p.m. and costs $3 per person or $10 for a family of four. The museum credits the Connecticut G-Scalers Club and The Housatonic Model Railroad Club for their support.
Santa's Arrival is the next morning at Sherman Green, according to the Fairfield Chamber's listing. It's free and runs from 10 a.m. to 2 p.m. It's the same green where the Sunday farmers market spent its summer and fall, a season we covered in September.
This means Santa makes two scheduled Fairfield appearances this month. The first is at the museum market on November 14, and the second is on Sherman Green on November 29. If one Saturday morning is already full, there's another chance two weeks later.
The grand opening is the busy night. The quieter visits come after it. The museum's calendar lists a Holiday Express session on Thursday, December 3, from 10 a.m. to 1 p.m., where model trains wind through winter villages and holiday scenes. A weekday morning is a good fit for preschoolers and for grandparents visiting over the holidays.
Two pricing details bring this back to the market's $5 donation. Museum members and children 5 and under get into the train show free. And people who join in December get 18 months of membership for the price of 12. That offer is for new members only. The market raffle prize is a family membership, so a household that wins on November 14 would have free train show visits all season.
The Fairfield Museum's event pages list the train show sessions, and they're the place to check before heading over on a given day.
Here's the season in order, from tomorrow through the first Thursday of December:
This is the first of the museum's two big holiday weekends, and it's tomorrow. If you're hosting family for the holidays or getting a home ready to sell while Fairfield is busy with the season, Jennifer Lockwood is glad to talk through timing. Request a complimentary market consultation and we'll plan around the dates that matter on your street.
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