When does Wilton's holiday season actually start? On paper, Friday, November 27, when the Wilton Historical Society opens its Great Trains Show at noon. The first real decision comes earlier, on Sunday, November 15. That is the last day to preorder a tree or wreath from Ambler Farm, and a preorder is the only way to choose a tree before the farm opens to the public.
As of Thursday, November 5, that window has ten days left. After it closes, the season moves fast. Nearly everything in town happens over two Friday-to-Sunday stretches. By the evening of December 6 the farm sale is over, and only the trains and the library carry the season into January.
The Window That Closes November 15
Ambler Farm's online preorder runs November 1 through November 15, 2026, for trees and wreaths. Pickup is Saturday, November 28, from 9:00 a.m. to noon, and the farm says this "allows you to choose your tree before we open to the public."
So a preorder placed now gives you three hours on the farm at 257 Hurlbutt Street before the gates open to everyone at noon. Ambler calls the Greens Sale "a beloved holiday event for so many families." The farm also describes hot cider, sweet treats, a fire, and the Ambler Shop selling farm gifts and syrup.
Ambler also lists the Greens Sale as one of its biggest annual fundraisers. It recruits volunteers to help shoppers, sell merchandise, run preorder pickup and load trees onto cars. The volunteer model goes back a while. In 2018, Good Morning Wilton reported that farm staff worked alongside volunteers from Lee Horticultural Services, KMG Landscaping and Wilton Lawn Service to unload trees, wreaths and roping for that year's sale.
Public sale hours after the preorder morning:
| Date | Hours |
|---|---|
| Saturday, November 28 | 12:00 p.m. – 4:00 p.m. |
| Sunday, November 29 | 11:00 a.m. – 4:00 p.m. |
| Saturday, December 5 | 9:00 a.m. – 4:00 p.m. |
| Sunday, December 6 | 11:00 a.m. – 4:00 p.m. |
That makes four public days in all, split across two weekends with nothing in between. The full schedule is on Ambler's Greens Sale page.
What Fills the Ten Days Before the Order Closes
The rest of the preorder window belongs to quieter programs, mostly outdoors and mostly at Woodcock Nature Center:
- Friday, November 6, 6:00 – 8:00 p.m. An Owl Prowl for grades 5 through 8, with a guided owl search and campfire activities.
- Saturday, November 7, 10:30 a.m. – 12:30 p.m. An open house to meet Woodcock's ambassador animals.
- Saturday, November 7, 1:00 – 2:30 p.m. A family hike about how reptiles and other creatures get through winter.
- Saturday, November 14, 10:30 a.m. – noon. A guided hike about forest decomposers, run with Wilton Land Trust.
That last hike falls on the day before the Ambler preorder closes. If you want first pick of a tree, the decomposers walk is the last weekend outing before the deadline.
Indoors, Wilton Library is showing "Weir Inspired: Works of the Weir Farm Artist Collective." The exhibition has work by more than 30 artists connected with Weir Farm's Artist Collective and runs through Thursday, November 19. That is four days after the preorder closes and eight days before the trains start.
Holiday programming at the library includes a cookie-decorating program for grades 4 through 7 on Tuesday, November 24, from 1:30 to 3:00 p.m., two days before Thanksgiving.
Thanksgiving Friday Starts Two Clocks at Once
The Great Trains Show opens on Friday, November 27, at noon. The next morning, Ambler's preorder pickup begins at 9:00 a.m. So the town's two main seasonal events open less than 24 hours apart. One lasts four days spread over two weekends. The other runs into January.
The Historical Society describes the show as running every year from the day after Thanksgiving through Martin Luther King Day. In 2027 that holiday falls on January 18. The show's roots go back decades. Good Morning Wilton counted 2013 as its 16th year and reported that residents had donated some of the layouts and equipment. That year the train committee put in more than 100 hours over several weeks.
The setting is the Society's 18th- and 19th-century buildings at 224 Danbury Road. Model train layouts wind through miniature towns with tunnels, buttons to push and volunteer "train engineers" on hand to talk trains. The lit winter village has skaters, sledders, horse-drawn wagons, swans and Ebenezer Scrooge in his gloomy house.
Admission is free for Historical Society members, $5 for each nonmember child and $10 for each nonmember adult. You can buy tickets at the door, or buy ahead online for faster entry.
The schedule has changed for 2026–27. The Society says it will no longer open on Wednesdays. Regular hours are now Thursday through Saturday, 10:00 a.m. to 4:00 p.m., and Sunday, noon to 4:00 p.m. Holiday week is the exception, with two weekday openings outside the usual pattern:
| Date | Hours |
|---|---|
| Thursday, December 24 | 10:00 a.m. – 1:00 p.m. |
| Friday, December 25 | Closed |
| Tuesday, December 29 | 10:00 a.m. – 4:00 p.m. |
| Wednesday, December 30 | 10:00 a.m. – 4:00 p.m. |
| Thursday, December 31 | 10:00 a.m. – 1:00 p.m. |
| Friday, January 1 | Closed |
Wednesday, December 30, is the only Wednesday of the season when the show is open.
The Second Weekend Puts Three Events on One Saturday
The Wilton Chamber of Commerce's Holiday Stroll 2026 is Friday, December 4, from 4:30 to 7:30 p.m. in Wilton Center, rain or shine. Kimco Realty is the sponsor, and the Chamber thanks the merchants and businesses that host receptions in their stores. The Chamber says the full lineup of festivities "will be available soon."
Saturday, December 5, is the busiest day of the season. Three events overlap:
- 9:00 a.m. Ambler Farm opens for its longest public sale day, running until 4:00 p.m.
- 10:00 a.m. The Great Trains Show opens for its regular Saturday hours, until 4:00 p.m.
- 2:00 – 3:00 p.m. The Historical Society hosts Polar Express Day, with a story reading, a keepsake craft and entry to the Great Trains Show. Registration is required.
The farm sale and the trains share six hours of overlap that day. Polar Express Day is the one event on the list that needs advance registration rather than a ticket bought at the door. Sunday, December 6, is the farm's last public day, from 11:00 a.m. to 4:00 p.m.
After December 6, the Season Moves Indoors
Once the Ambler sale ends, Wilton's season runs on two indoor venues. Wilton Library's Holiday Book Sale, which opens between the two farm weekends on Monday, November 30, at noon, continues through Sunday, January 3, at 5:00 p.m. The library also offers a holiday charcuterie-board class on Tuesday, December 8, from 6:30 to 8:00 p.m. The Great Trains Show stays open on its Thursday-through-Sunday schedule until Martin Luther King Day.
The Historical Society also points visitors to its Shop and Dine Local guide, which lists partner businesses for anyone making a full day of a trains visit.
Three dates carry the season's timing risk: the November 15 preorder close, the Wednesday closures at the trains in every week except the one between Christmas and New Year's, and December 6, the farm's last public sale day.
A town's own calendar says a lot about how a place runs, and that kind of local knowledge also shapes how we advise clients who are weighing a move between Manhattan and Fairfield County. If you're planning a sale or purchase around Wilton's seasons, William Martin can walk you through the timing. Request a private, investment‑grade consultation.
