New Canaan's 2026 holiday calendar starts two weeks ahead of the first Friday in December. On Friday, Nov. 20, the Town Players open "Rudolph the Red-Nosed Reindeer" at Waveny Park. On Saturday, Nov. 21, the New Canaan Nature Center holds its Holiday Market. On Sunday, Nov. 22, the Turkey Trot starts at the Waveny Main House. That's three events opening within about 40 hours.
The other end of the season comes up fast too. "Rudolph" closes Dec. 13, Grace Farms is open only to ticketholders that same day, and the Glass House ends its tour season on Dec. 14. That leaves about three and a half weeks of holiday calendar, and it starts the weekend before Thanksgiving.
The first half of November still belongs to America250
Before the holiday programming starts, early November is taken up by the town's anniversary year. The Town of New Canaan's America250 program runs through Veterans Day, Wednesday, Nov. 11, and includes more than 40 events covering history, music, theater and community activities. The Tuesday before, the New Canaan Museum & Historical Society hosts Election Day Family Fun on Tuesday, Nov. 3, from 11 a.m. to 1:30 p.m., with children's activities and museum tours.
Holiday-themed programs start to appear in this stretch, but on their own. Silvermine Arts Center opens its Holiday Salon, "The Gift of Art," on Saturday, Nov. 7, and keeps it up through Dec. 23. The New Canaan Library hosts "Cooking Demo: Holiday Side Dishes" on Nov. 1 and "Cooking Instruction: Chef Julia Deane Makes Holiday Appetizers" on Nov. 10. On Sunday, Nov. 15, Grace Farms presents violinist Nemanja Radulović with Double Sens.
Each of these is a single event on its own date. Holiday events don't start stacking up until Nov. 20.
Forty hours that open the season
The Nature Center calls its market the event that will "kick off the holiday season," and the rest of the weekend lines up behind it. Here's the order things happen in:
- Friday, Nov. 20, 2 to 4 p.m. The New Canaan Library runs "Cricut Crafts for Adults: Winter Holiday Bookmarks." Registration is required.
- Friday, Nov. 20, 3 to 5 p.m. Early Turkey Trot check-in opens at the Library.
- Friday, Nov. 20, 7 p.m. "Rudolph the Red-Nosed Reindeer" opens at the Powerhouse Theatre in Waveny Park.
- Saturday, Nov. 21, 10 a.m. to 5 p.m. The Nature Center Holiday Market runs at 144 Oenoke Ridge. Admission is free.
- Saturday, Nov. 21, 10 a.m. to 1 p.m. A second Turkey Trot check-in window is open at the Library.
- Saturday, Nov. 21, 10:30 a.m. to noon. Grace Farms offers a $30 tour, listed on the New Canaan Chamber of Commerce calendar.
- Saturday, Nov. 21, 7 p.m. "Rudolph" has its second performance.
- Sunday, Nov. 22, 11:30 a.m. The Turkey Trot starts at the Waveny Park Main House, 899 South Ave.
- Sunday, Nov. 22, 2 p.m. "Rudolph" plays its first matinee.
- Sunday, Nov. 22, 3:30 to 4:30 p.m. The Library runs "Art Class for Grades 3-5: Thanksgiving Suncatchers." Registration is required.
Waveny Park hosts both ends of the weekend: the theater opening on Friday night and the race and matinee on Sunday. The Library on Main Street links them, since Turkey Trot runners pick up their check-in there on Friday afternoon or Saturday morning.
Waveny on Sunday morning
The Turkey Trot describes itself as a short run through Waveny Park "the Sunday before the holiday." The 5K course starts and finishes at the Main House. Race-day check-in opens at 10:30 a.m., an optional group warm-up and kickoff starts at 11, and the race begins at 11:30. All proceeds go to Open Doors Shelter in Norwalk. Once the race is done, there's still time before the 2 p.m. "Rudolph" matinee at the Powerhouse Theatre, which is also in the park.
Rudolph at the Powerhouse Theatre
The Town Players of New Canaan are staging Robert Penola's adaptation of the 1964 stop-motion special, with music and lyrics by Johnny Marks. The show includes Hermey the Elf, Yukon Cornelius, the Bumble and "A Holly Jolly Christmas." It runs 90 minutes. Tickets are $40 for adults, $35 for seniors and $25 for students, and an Angel tier costs $100. The run lasts until Dec. 13, so later dates are available for anyone who misses opening weekend.
The Nature Center market
The Holiday Market lasts all day Saturday and admission is free. Vendors sell jewelry, clothing, candles and other gifts, and School of Rock plays holiday music. It's the most flexible stop of the weekend, with a seven-hour window that fits around a Grace Farms tour in the morning and the "Rudolph" curtain at 7 p.m.
Thanksgiving week goes quiet in one specific place
After that weekend, the calendar pauses for Thanksgiving. The Glass House is closed Nov. 26 to 28, Thursday through Saturday, in addition to its regular Tuesday and Wednesday closures. That means the site doesn't run tours from Tuesday, Nov. 24, through Saturday, Nov. 28. That matters for anyone who planned to take visiting family on a tour over the long weekend.
Grace Farms fills the Saturday. Its Nov. 28 calendar lists an all-day Holiday Market pop-up with gifts that give back, including art sets, toys and treats. The same day has a 10 a.m. children's open arts studio and a 10:30 a.m. tour of the River building and Barns.
Three weeks, then the institutions close their year
From Thanksgiving on, the season is mostly about final dates. The Glass House changes its hours for the last stretch. All tours start and end at the Visitor Center and Design Store at 199 Elm Street. In November and December the last tour of the day leaves at 2:30 p.m., compared with 3:45 p.m. on most days through October. Tours run Sunday, Monday, Thursday, Friday and Saturday. Children must be at least 8 years old. The Glass House recommends reserving ahead, since tours often sell out.
The Holiday Stroll fits into this window. The Chamber of Commerce describes it as held on the first Friday evening in December. In 2026, the first Friday is Dec. 4, and "Rudolph" has a 7 p.m. performance that night. The Chamber hasn't posted the 2026 Stroll date yet, so check its calendar before making plans around that evening.
The closing calendar
- Saturday, Dec. 5: Grace Farms tour, 10:30 a.m. to noon, $30. "Rudolph" at 2 and 7 p.m.
- Sunday, Dec. 6: Grace Farms cookie decorating at 1 and 3 p.m., with sugar cookies provided. "Rudolph" matinee at 2 p.m.
- Sunday, Dec. 13: "Rudolph" closes. Grace Farms hosts Broadway Inspirational Voices, and the site is open only to event ticketholders that day.
- Monday, Dec. 14: The Glass House ends its 2026 tour season.
- Wednesday, Dec. 23: Silvermine's Holiday Salon ends, more than a week after the others.
Dec. 13 and 14 effectively close the season. On Sunday the 13th, the Town Players finish their run and Grace Farms is open only for its ticketed concert. On Monday the 14th, the Glass House runs its last tours. After that, Silvermine's salon is the only one of these programs still running. This year's Glass House season opened April 16.
For anyone counting backward from those dates, the weekend of Nov. 20 to 22 has the widest choice of the whole stretch. A play, a market, a race, a Grace Farms tour and Library programs for both adults and kids all happen over three days, before Thanksgiving week closes the Glass House and the December dates start filling in.
If the holiday weeks have you thinking about how your home will look when you list it in the new year, Taylor Tait can walk through it with you, from staging to timing. Request a complimentary home valuation and start planning for the spring market.
