How long does New Canaan's holiday season last? The lampposts on Elm Street say it runs from Thanksgiving through January, about nine weeks in all. The calendar is shorter. From Friday, December 4, through Monday, December 14, the town fits in the Holiday Stroll, a Saturday with Santa, the Grace Farms Holiday Market, a cookbook talk at the library, a Broadway gospel concert and the Glass House's last tour day of the year. The lights stay on for about seven weeks after the last of those dates.
Mid-November is a good time to plan, because two of the season's dates come with deadlines, and one of them falls before Thanksgiving.
The First Deadline Comes Before the First Light
The New Canaan Chamber of Commerce's lamppost campaign covers more than 75 downtown lampposts. Each one gets green garland, white lights and a personalized name tag tied with a red bow. A sponsorship costs $250 and keeps a family or business name on Elm Street from Thanksgiving through January. Businesses can ask for a post near their own storefront or office.
The deadline is Wednesday, November 18, and the Chamber says spots fill quickly each year. The sponsorships also help pay for the Holiday Stroll. So the decorations that go up at Thanksgiving help fund the event that opens the December stretch.
November Is the Quiet Half, and It Happens Away From Elm Street
Before downtown fills up, November's events are spread across town and spaced out.
- Saturday, November 7, 11 a.m. to noon. Horticulture specialist Michael Poulin leads a garlic-planting workshop at Grace Farms, 365 Lukes Wood Road. Participants go home with a garlic head to plant.
- Tuesday, November 10, 11 a.m. to 1 p.m. Chef Julia Deane teaches holiday appetizers at the New Canaan Library.
- Sunday, November 15, 3 to 4:45 p.m. Violinist Nemanja Radulović and the chamber ensemble Double Sens perform at Grace Farms as part of the ensemble's U.S. debut tour.
The Glass House has its own calendar to watch in November. The site is closed Thursday through Saturday of Thanksgiving week, November 26 to 28, and it is closed every Tuesday and Wednesday all season. If you're planning a Thanksgiving visit with out-of-town family, that leaves Sunday, November 29, as the first open day after the holiday.
The Glass House Runs on a Shorter Winter Day
The Glass House visit page lists April 16 through December 14 as the 2026 tour season. Monday, December 14, is the last day, and the hours shrink on the way there.
- Every tour starts and ends at the Visitor Center + Design Store at 199 Elm Street, and a shuttle takes visitors to the site.
- From April through October, the last tour left at 3:45 p.m. on most days. In November and December, the last tour leaves at 2:30 p.m.
- Self-guided tours aren't offered in November or December.
- Tours go out rain or shine. Every ticket sale is final, with no refunds or date changes, and advance reservations are strongly recommended because tours often sell out.
For November and December, the last departure on Monday, Thursday, Friday and Saturday is 75 minutes earlier than it was through October. With the site closed every Tuesday and Wednesday and for three days at Thanksgiving, the stretch from November to December 14 has fewer tour days than the calendar suggests. One Friday and one Saturday with tours fall during Stroll weekend.
Three Days, Two Addresses: December 4 to 6
The Chamber's 2026 Stroll announcement says a group of local merchants started the event 22 years ago. It calls the Stroll "New Canaan's answer to 'Small Business Saturday'." This year the Stroll begins one weekend and runs into a second event across town.
| Day | Time | Where | What |
|---|---|---|---|
| Friday, December 4 | 5:30 to 8:30 p.m. | Downtown | The Holiday Stroll, with shopping, food, a show by young local performers and photos with Santa and Mrs. Claus |
| Saturday, December 5 | 10 a.m. to 3 p.m. | 161 Elm Street | Santa returns for younger children, with a magician making balloon animals for kids waiting in line |
| Sunday, December 6 | Noon to 5 p.m. | Grace Farms, 365 Lukes Wood Road | Holiday Market with art sets, toys, teas, coffees, handmade ornaments and artisan embroidery |
The Chamber's own wording differs in two places. The Stroll announcement calls it "the weekend after Thanksgiving," but the dates it gives, December 4 and 5, fall on the second weekend after the holiday. The lamppost page describes the Stroll as a two-day event on Friday and Saturday. Either way, the dates are the same in both places: the Stroll runs Friday night and Santa comes back Saturday daytime. The Chamber's standing annual-events page lists the Stroll on the first Friday evening of December and the Santa visit on the first Saturday, so 2026 keeps the usual pattern.
On Friday, December 4, the Glass House's last tour leaves 199 Elm Street at 2:30 p.m. The Stroll starts on the same street three hours later. That leaves time for an afternoon tour and the Stroll on the same day, with a gap in between.
Two Downtown Shops That Weren't Open Last December
Two women's clothing shops near Elm Street opened after last year's Stroll.
Dry Martini Clothing is a Manhattan-based women's fashion brand. It opened its second location, at 78 Elm Street, on September 12. The NewCanaanite story on the opening gives the address as 70 Elm Street in the text and 78 Elm Street in the photo caption. The Chamber's directory lists 78. Designer Sarah Miller told NewCanaanite she wanted "to create clothes that feel alluring without being revealing."
Kset, a women's clothing shop, opened on Elm Street earlier this year. It has since moved around the corner to 6 South Ave., at Morse Court. Owner Kristen Setter buys the stock herself at trade shows in New York and Las Vegas, aiming at women from high school and college age through their 20s. She told NewCanaanite that the space is "a stepping stone, and I hope in the future I will be permanently in New Canaan, too." Because Kset calls this location a stepping stone, there's no guarantee the shop will still be at that corner next December.
The Week After the Stroll Closes the Calendar
The first weekend in December starts the busy stretch. The week after it wraps up the events.
- Tuesday, December 8, 1 to 2 p.m. Cookbook author Caroline Schiff speaks at the New Canaan Library. The Glass House is closed Tuesdays, so this is one of the few afternoons that week without a tour option.
- Sunday, December 13, 3 to 4 p.m. Broadway Inspirational Voices brings 30 vocalists to Grace Farms for a family-friendly program of Christmas, Broadway and gospel music. Grace Farms says this is the choir's second straight year performing the program there.
- Monday, December 14. This is the Glass House's last tour day of 2026, with the final departure from 199 Elm Street at 2:30 p.m.
After December 14, nothing else is on this calendar, but the Chamber's lamppost lighting runs through January. That leaves about seven weeks of lights after the last scheduled event.
Bob Virgulak works in New Canaan all year, on both the residential side and the commercial side of the storefronts that light up on Stroll night. If you'd like to talk about how downtown New Canaan is changing, from new Elm Street shops to the buildings around them, contact Bob Virgulak to Request a Market Consultation.
