The Westport Farmers' Market's Winter Calendar Turns on Three Holiday Thursdays

"Fresh, local food doesn't take a winter break, and neither do we," Westport Farmers' Market executive director Lori Cochran-Dougall told 06880 before the market moved indoors. In the same piece she described "walking into those warm greenhouses on a cold morning, and watching the community gather around good food when the rest of the world has gone quiet."

This year the holiday weeks will be anything but quiet on the calendar. The winter market at Gilbertie's Herbs & Garden Center is built around Thursdays. In 2026, Thanksgiving, Christmas Eve and New Year's Eve all land on a Thursday. In recent winters the market has kept its holiday-week markets but moved them to a Monday or Tuesday. So between now and January, the weeks when a fridge full of local produce matters most are the weeks most likely to break the usual routine.

Fifteen Days Earlier Than Last Winter

The move to 7 Sylvan Lane happened on Thursday, Nov. 5. Vendors now fill three heated greenhouses every Thursday and on the first Saturday of each month, 10 a.m. to 2 p.m., through March 11. The market's own announcement promised "a great variety of local seasonal produce and prepared food, more programming, and heating to keep you cozy while you shop all winter long." A day earlier, its Instagram feed said shoppers would find "all your favorite vendors" at the new site.

Last winter the market didn't open at Gilbertie's until Nov. 20, 2025, according to 06880's announcement that season. This year's Nov. 5 start comes 15 days sooner. The weeks between the last outdoor market on Imperial Avenue and the first indoor one have mostly closed up. Two of those extra Thursdays fall in the run-up to Thanksgiving.

The monthly Saturday market is in its second winter. It began last season "in response to community feedback," with Saturday dates on Dec. 6, Jan. 3, Feb. 7 and March 7. It returned this year without changes.

All of this comes at the end of a big year for the market. Paul Newman and Michel Nischan founded it in June 2006. Its 20th summer brought recognition from the United States Senate, new programs and, at last, a restroom at the Imperial Avenue lot. In an Oct. 27 farewell post to the summer site, Cochran-Dougall welcomed it as "Girdie."

Three Thursdays That Have Moved Before

Thanksgiving falls on Thursday every year, so the market has a long record of handling that week. The December holidays are the variable. In 2026 both Christmas Eve and New Year's Eve fall on Thursday, and the most recent comparable years show the market moving those weeks to another day too.

• Thanksgiving 2022: The market held a special Tuesday, Nov. 22 session in place of the Thursday that week, as Westport Journal reported.
• Thanksgiving 2023: A Tuesday, Nov. 21 holiday market took place in the Gilbertie's greenhouses, which Westport Journal previewed.
• Christmas and New Year's 2024: The market ran on Monday, Dec. 23 and Tuesday, Dec. 31, then "back to normal: Thursdays, through mid-March," 06880 told readers.
• Thanksgiving 2025: The pre-Thanksgiving market was set for Tuesday, Nov. 25, and the market was closed on the holiday. Featured items included fresh produce, meats, desserts, flowers and pet food.
• New Year's week 2025: 06880 listed a Tuesday, Dec. 30 market at Gilbertie's, 10 a.m. to 2 p.m.

The pattern holds across four seasons. When a holiday falls on market day, the market usually moves earlier in the week instead of skipping it. In 2024, the last year the calendar fell this way at the end of December, that meant a Monday market before Christmas and a Tuesday market on New Year's Eve. The day for each holiday week is posted on the market's site and on Instagram at @westportfarmersmarket. Check there before planning a Thanksgiving shop around a Thursday morning.

The Season, Laid Out Through March 11

The table below lays the published cadence over the 2026–27 calendar. The middle column shows each holiday Thursday as it falls this year. The right column shows how the market handled the same week in recent seasons.

Taken together, the holiday weeks and the first Saturdays leave three regular Thursday markets in December, on Dec. 3, Dec. 10 and Dec. 17. The second half of the month is where the schedule moves around.

Dec. 5 Puts the Market and the Holiday Stroll on One Saturday

The first Saturday of December would be a market day anyway. This year it is also the date of the 6th annual Holiday Stroll, which 06880 co-sponsors with the Westport Downtown Association. The two events run at different hours in different parts of town, so one Saturday can hold both:

1. 10 a.m. to 2 p.m., Gilbertie's, 7 Sylvan Lane. First-Saturday winter market in the greenhouses.
2. 4 to 7 p.m., downtown. Main, Elm and Church Streets fill with the Staples Orphenians, a string ensemble, a DJ, Santa, face painting, a photo booth, vendors, nonprofits, and merchant and restaurant promotions, some with freebies. The WDA lists the Elm + Main lot as the event hub.
3. During the Stroll. Dec. 5 is the second night of Hanukkah, so the program includes a menorah lighting with Chabad of Westport.

The WDA says the Stroll map, vendor lineup and live-music details will follow on its event page. Local businesses that want to take part can sign up through the form linked in 06880's Oct. 26 roundup.

Why the Host Site Suits a Holiday Market

Gilbertie's isn't a neutral venue for these weeks. The Westport garden center dates to 1922 and has been family-owned for four generations. Its own seasonal stock runs to Christmas trees and holiday décor, along with the organic herbs, houseplants, succulents and pottery it sells year-round. That means a trip for produce in December puts shoppers at a place that sells trees, wreaths and decorations too.

The market has run its biggest holiday sessions in these greenhouses before. The Tuesday market before Thanksgiving 2023 brought farms including Fort Hill Farm, Cloudy Lane, Riverbank Farm, Ox Hollow Farm, Woodland Farm, Sport Hill Farm and Muddy Feet Flower Farm, according to 06880's vendor list. Food vendors that day included Wave Hill Breads, Kneads Bakery, Calf & Clover, Seacoast Mushrooms, Farmers & Cooks, Boxcar Cantina and Badass Bagels. Each season's lineup changes. Still, that list shows how much a single holiday session can hold: bread, mushrooms, flowers and prepared food under one heated roof.

Last winter's announcement also promised kids' activities, music, food trucks and holiday pop-ups in the greenhouses. This year the market has promised "more programming" than before. With the indoor season now 15 days longer, that programming has more Thursdays to fill before the holidays start moving the schedule.

The next regular Thursday market at Gilbertie's runs 10 a.m. to 2 p.m., and the final one of the season falls on March 11. Our team at Katie O'Grady & Team follows these details across Westport and the rest of Fairfield County. If you're thinking about selling a Westport home this winter, we'd welcome the chance to talk it through. Schedule a complimentary listing consultation, and we'll walk you through how the season ahead may shape your timing.