On the Saturday after Thanksgiving, at 4:45 p.m., a Fairfield resident chosen by the town will light the tree on Old Town Hall Green. Fifteen minutes after the ceremony starts, the Fairfield Museum and History Center at 370 Beach Road opens its Holiday Express Train Show. The museum's event page invites people to "warm up at the Fairfield Museum after the town's tree and menorah lighting ceremony."
The museum timed its opening to the town's lighting on purpose, and it works that way all season. The museum also starts the season two weeks before Thanksgiving, and it is still running trains on December 12, when much of the rest of the town's December calendar lands.
The Museum Gets There First
The first holiday event on the calendar is the Fairfield Museum's 12th annual Holiday Pop-Up Market, on Friday, November 13, from 4 to 7 p.m. and Saturday, November 14, from 10 a.m. to 4 p.m. Friday evening includes a wine-and-cheese reception.
According to the museum's market listing, the vendors include The Perfect Page, Lovely Chocolate LLC and Salt & June Jewelry, and The Inclusive Brew will serve coffee and seasonal drinks outside on Saturday. Admission is a $5 donation.
Santa shows up early, too. He is scheduled at the market on Saturday, November 14, from 10 a.m. to 12:30 p.m., and the museum says children 12 and under can visit him for free. That makes it the first Santa visit of the Fairfield season, more than two weeks before the Chamber of Commerce brings him to Sherman Green.
A Resident Lights the Tree
Two days after the market, the town closes nominations for the person who will light the tree. Fairfield Parks and Recreation is taking nominations through Monday, November 16, 2026, using its tree lighting nomination form.
The form sets out the rules:
- Candidates must be Fairfield residents, or from Fairfield if they are serving in the military abroad.
- If the person chosen is serving abroad, a family member can light the tree on their behalf.
- Forms can be mailed to Fairfield Parks and Recreation at 75 Mill Plain Road, faxed to 203-256-3145, or emailed to the address listed on the form. The department's phone number is 203-256-3191.
Because of this setup, the person at the switch on November 28 is a neighbor, picked from the town's own nominations, and is being honored for something done here.
4:45 on the Green, 5:00 at the Museum
Thanksgiving weekend packs three events into about 21 hours, and they all sit on or just off the Post Road.
| When | What | Where | Cost |
|---|---|---|---|
| Sat., Nov. 28, 4:45 p.m. | Tree and menorah lighting | Old Town Hall Green | Not listed |
| Sat., Nov. 28, 5 to 7 p.m. | Holiday Express Train Show grand opening | Fairfield Museum, 370 Beach Road | $3 per person, $10 per family of four |
| Sun., Nov. 29, 10 a.m. to 2 p.m. | Santa's Arrival Fairfield | Sherman Green, Post Road and Reef Road | Chamber community event |
The train show's opening-night price of $3 a person, or $10 for a family of four, makes it one of the cheapest indoor stops of the season. The museum's grand opening page credits support from the Connecticut G-Scalers Club and the Housatonic Model Railroad Club. The museum's December listings describe the display as model trains winding around winter villages and holiday scenery.
Visitors who come over from the lighting at 5 p.m. are, in the museum's words, "one of the first to see" the layouts.
Sunday Moves Up the Post Road
On Sunday the season moves to Sherman Green, at the corner of Post Road and Reef Road, listed at 1451 Post Road. The Fairfield Chamber of Commerce runs Santa's Arrival there from 10 a.m. to 2 p.m. on Sunday, November 29.
The Chamber also uses the event to raise money for local groups. Its event page invites nonprofits, scout troops and school groups that want to fundraise at the event to call the Chamber office at 203-255-1011. It also asks holiday shoppers to "Shop Local" and support Fairfield's merchants, retailers and restaurants.
Kneads, a new bakery-café at 1916 Post Road, is a short trip up the road for anyone heading out early. Patch reported in October that the shop, owned by Daniel and Brittany Moreno, makes its breads and pastries from scratch with ingredients from regional grain producers, serves coffee, breakfast and lunch, and sells organic flour. At the time, Patch listed weekend hours of 8 a.m. to 3 p.m., which covers the whole Santa window on Sherman Green.
The Trains Keep Running Into December
After opening weekend, the museum posts the train show's hours one day at a time. The posted December dates are Sunday, December 6, from 10 a.m. to 4 p.m.; Friday, December 11, from 10 a.m. to 1 p.m.; and Saturday, December 12, from 10 a.m. to 4 p.m.
Two of those dates line up with Fairfield's busiest December performance days, which makes the museum a natural first stop:
- Friday, December 4, 7:30 p.m. The Fairfield University Glee Club performs A Feast of Carols at the Quick Center.
- Sunday, December 6, 3 p.m. Mark O'Connor brings An Appalachian Christmas to the Quick Center. The train show is open that day until 4 p.m.
- Saturday, December 12, 6 p.m. Connecticut Dance opens its Nutcracker run at the Quick Center. The train show closes at 4 p.m. that day.
- Saturday, December 12, 7 p.m. Shakespeare on the Sound stages a benefit reading of A Christmas Carol at Pequot Library, 720 Pequot Avenue in Southport. Tickets are $75 for adults and $25 for children under 12, and the organizer says light food and drinks are included.
- Sunday, December 13, 1 p.m. and 4 p.m. The Nutcracker has two more performances, and the 1 p.m. show is sensory-friendly.
That puts December 12 second only to Thanksgiving weekend for how much is packed into one day. The museum's layouts are open through the afternoon, the Nutcracker starts at 6, and the Pequot Library reading starts an hour later in Southport. The Quick Center's 2026-27 season calendar has ticket links for its three December programs.
The sensory-friendly Nutcracker on the afternoon of December 13 gives families who want a quieter performance their own time slot on the same weekend.
If you're thinking about a home within walking distance of Old Town Hall Green, Sherman Green or Southport, McGrath Realty can tell you how those blocks compare across Fairfield County.
