On Friday, December 4, the New Canaan Chamber of Commerce will light up downtown for its Holiday Stroll, from 5:30 to 8:30 p.m., with shopping, performances by young local talent, food, and Santa and Mrs. Claus. By then the Silvermine Arts Center's Artisan Market will have been over for nearly four weeks. The New Canaan Nature Center's market will be thirteen days in the past. Grace Farms will be on the second week of its holiday pop-up, and the Carriage Barn will be two days into its own holiday market.
The town's gift season this year moves through its arts and nature institutions first, from Silvermine Road to Oenoke Ridge to Lukes Wood Road to Waveny Park. Elm Street is the last stop to open. If you wait for the Stroll to start buying, you'll have missed half the calendar.
Six Openings Over Four Weeks
Here is the season in the order it opens, from Silvermine on November 7 to Elm Street on December 4.
| Opens | Venue | Event | Hours | Cost |
|---|---|---|---|---|
| Sat., Nov. 7 | Silvermine Arts Center, 1037 Silvermine Road | Artisan Market, Nov. 7–8 | 11 a.m. to 4 p.m. | Free |
| Sat., Nov. 7 | Silvermine Arts Center | Holiday Salon, through Dec. 23 | Tue.–Sat., 10 a.m. to 4 p.m. | Not listed |
| Sat., Nov. 21 | New Canaan Nature Center, 144 Oenoke Ridge | Holiday Market | 10 a.m. to 5 p.m. | Free |
| Fri., Nov. 27 | Grace Farms, 365 Lukes Wood Road | Holiday Market, 12 dates through Dec. 10 | During regular visitor hours | Free with daily registration |
| Wed., Dec. 2 | Carriage Barn Arts Center, Waveny Park, 681 South Ave. | Deck The Walls Small Works Exhibition & Holiday Market, through Dec. 18 | Wed.–Sat., 10 a.m. to 3 p.m.; Sun., 1 to 5 p.m. | Not listed |
| Fri., Dec. 4 | Downtown | Chamber Holiday Stroll | 5:30 to 8:30 p.m. | Not listed |
The Glass House is the other date to know. Its 2026 tour season ends Monday, December 14.
November 7 Sets the Pace for Everything After It
Silvermine opens the season with two things on the same Saturday. The Artisan Market runs November 7 and 8, 11 a.m. to 4 p.m., with free admission and more than 20 makers working in textiles, jewelry, wood, glass, paper and ceramics. The vendor list is specific enough to shop from in advance:
- Candles: Oh D' Luxe, Tug Hill Candles
- Ceramics: Janis Cutler Gear, Zach Dunn, Jon Puzzuoli, Barbara Scioscia-Reed
- Glass: Papineau Studio, Soda Glass House
- Wood: Holm-Hansen Woodturning, Solder and Grove
- Paper and prints: Mount Cornwall Book Bindery, Leslie Giuliani
- Jewelry: Denisse Aneke Jewelry, Lee Skalkos Jewelry, Dara Saol, Emmy Starr, Sabrina Furst Designs, Serena Van Rensselaer, Lydia Tucci
- Textiles and accessories: Altered States Designs, Heike NY, Knots on Euclid, Lalaa Kanani Block Prints
The Holiday Salon – The Gift of Art opens the same day and stays up through December 23. It's a show of original work by Silvermine's Guild Artists, from paintings and sculpture to prints and ceramics, and the art goes home with the buyer straight off the walls. Gallery and store hours are Tuesday through Saturday, 10 a.m. to 4 p.m. The market lasts one weekend, but the Salon gives Silvermine the longest holiday window of any venue on the calendar, starting four weeks before the Stroll and ending on December 23, the day before Christmas Eve.
That evening, the Center for Contemporary Printmaking holds its 2026 MONOTHON Auction & Party at the Carriage Barn Arts Center in Waveny Park, 5 to 8 p.m. The event is ticketed. The NewCanaanite event listing puts the ticket price at $65 and describes silent and live auctions. If you'd like to see the prints before the bidding starts, the Monothon exhibition is on view at the Carriage Barn on Thursday and Friday, November 5 and 6, from 10 a.m. to 3 p.m.
One more option falls on publish day itself. Tonight, Thursday, November 5, the New Canaan Museum & Historical Society hosts its third annual wine tasting with Francos Wine Merchants at 13 Oenoke Ridge, 6 to 8 p.m. Tickets are $20 for members and $40 for nonmembers. Five days later, on Tuesday, November 10, the Museum holds a noon Lunch & Learn with Vanessa Wood on the artist Augusta Simon.
Thanksgiving Weekend Belongs to Oenoke Ridge and Lukes Wood Road
After Silvermine, the season moves north of downtown. Grace Farms' Autumn Stroll on Saturday, November 14, is a guided walk with the Garden Team through the 80-acre landscape. It's ticketed, and it's a good preview of where the season's longest-running market will be held two weeks later.
On Saturday, November 21, the New Canaan Nature Center Holiday Market runs from 10 a.m. to 5 p.m. with free admission. The center bills it as the start of its holiday season, with jewelry, clothing, candles and other gifts, and School of Rock playing holiday music. Vendors include The Riverfield House, Arm Candy Collection, Portraits, Inc. – Elizabeth Ker, and A Girl And A Cupcake.
Six days later comes Thanksgiving weekend, the one built nationally around Small Business Saturday. In New Canaan, the posted calendar fills it with the Grace Farms Holiday Market. It opens Friday, November 27, and runs on twelve dates: November 27 through 29, December 1 through 6, and December 8 through 10. Grace Farms describes it as a limited-time pop-up held during regular visitor hours. Those hours are 10 a.m. to 5 p.m. Tuesday through Saturday and noon to 5 p.m. on Sunday, so the two Sunday dates, November 29 and December 6, open later. The market is free with daily registration, made through Grace Farms' visit scheduling.
The stock leans toward family gifts and host gifts: art sets, toys, treats, mugs, teas, coffees, books, notecards and memberships. It also carries handmade ornaments and embroidered works by Nasreen Sheikh, presented with the Empowerment Collective. Opening day includes Stories of the Season, a family storytime with Kate and Jake Goldbas in the Sanctuary from 11 to 11:45 a.m. The featured books will be for sale at the market. The Chamber calendar lists a second session that afternoon, 1 to 1:45 p.m.
Downtown Opens With Everything Else Already Running
The first week of December is where the institutional run and downtown overlap. On Wednesday, December 2, the Carriage Barn opens Deck The Walls, its Small Works Exhibition & Holiday Market. It stays up through December 18, open Wednesday through Saturday from 10 a.m. to 3 p.m. and Sundays from 1 to 5 p.m.
Two days later, the Stroll arrives. A group of local merchants started it 22 years ago, and the Chamber's announcement calls it the town's answer to Small Business Saturday:
"The Stroll functions as New Canaan's answer to 'Small Business Saturday', reminding all of us to 'think local first' when shopping for friends and family this Holiday season!"
That line comes from the Chamber's 2026 save-the-date, which also invites young families back on Saturday, December 5, from 10 a.m. to 3 p.m. Santa will be on Elm Street, and a magician will make balloon animals for children waiting in line.
On the night of the Stroll, Silvermine's Salon, Grace Farms' market and Deck The Walls are all open at once. Downtown joins a season that's already well underway.
Ten days later, on Monday, December 14, the Glass House closes its 2026 tour season. Its Visitor Center and Design Store at 199 Elm Street keep tour-season hours until then: Monday and Thursday through Sunday, 9:30 a.m. to 5 p.m., closed Tuesday and Wednesday. From January through mid-April, the Design Store is open by appointment only. The Glass House has no parking at the Visitor Center. It recommends the Lumberyard Lot, a municipal lot at 244 Elm Street that's free after 10:30 a.m., about a five-minute walk away.
The Season, Weekend by Weekend
- November 5–8. Wine tasting at the Museum on Thursday. The Monothon prints are on view Thursday and Friday. Saturday has the Silvermine Artisan Market and the Holiday Salon opening by day, then the MONOTHON party at the Carriage Barn that evening. Sunday is the market's last day.
- November 14. Autumn Stroll at Grace Farms.
- November 21. Nature Center Holiday Market, 10 a.m. to 5 p.m.
- November 27–29. Grace Farms Holiday Market opens Friday, with storytime in the Sanctuary. Sunday opens at noon.
- December 2–6. Deck The Walls opens Wednesday. The Holiday Stroll is Friday evening, with Santa on Elm Street Saturday. Grace Farms runs all week except Monday.
- December 8–14. Grace Farms' final market dates are Tuesday through Thursday. The Glass House season ends Monday the 14th.
- Through December 23. Silvermine's Holiday Salon and, through the 18th, Deck The Walls, for whatever is still left on the list.
If this calendar has you thinking about which part of town puts Silvermine Road, Oenoke Ridge or Elm Street within easy reach, Carla Kupiec can walk you through how those corners of New Canaan differ. Schedule a private consultation.
