"At this point, we have no plans to return to the Middle School." That line sits in the FAQ of the Pleasantville Farmers Market, under a question that longtime shoppers asked for years: will the winter market go back indoors? The answer is a settled no. Last December the Village made a similar decision about its holiday sing and tree lighting and moved it outside to the north end of Memorial Plaza, with a synthetic ice rink.
Those two decisions were made separately, but they point the same way. Pleasantville's busiest winter weekends now happen in the open air on the same stretch of pavement, and the 2026 calendar keeps building on that.
A market that tried the cold and decided to stay
A decade ago the winter routine looked very different. A 2015 Patch notice gave that year's schedule: a last outdoor market on November 21, a dark Saturday on November 28, and an indoor market opening December 5 at Pleasantville Middle School. By this point in November, the tents would have been about to come down.
The market moved outside in the winter of 2020 for safety reasons during the pandemic. According to its own FAQ, the outdoor winter market "has proven to be popular with our community, our farmers, and our volunteers," and the Middle School is no longer part of the plan. The market's visit page now describes it as outdoors all year at 10 Memorial Plaza.
Staying outside meant changing a few things for winter:
- Hours shorten after December. The market runs Saturdays from 8:30 a.m. to 1 p.m. from April through December, then 9:30 a.m. to noon from January through March. Opening an hour later and closing an hour earlier keeps the winter market to two and a half hours.
- Weather can cancel a Saturday. The FAQ says plainly that some days the weather won't allow the market to open, and that the shorter hours and quicker service are meant to cut down the time everyone spends in the cold.
- Market Bucks stop in January. The $5 and $10 market coins, which every vendor accepts and which save a trip to an ATM when a vendor doesn't take cards, are sold at the Manager's Tent only from April to December. If you rely on them, December is the last month to buy them before spring.
Those changes add up to a market built to keep going through the cold.
Who is still at the market as the weather turns
The vendor roster doesn't shrink to nothing in the cold months. The market's vendor profiles list Six Dutchess Farm as "weekly in winter," so it is a regular presence after the holidays, not a fair-weather one.
The vendor page also posts visit dates for guest vendors. The listings give a month and day but no year, and the November dates fall on Saturdays this year:
- Living Edge Designs on 11/7, 11/14 and 11/21
- Alpacatrax on 11/14, after a 10/24 visit
If those listings carry over to this season, November 14 has both vendors at once. The page also lists The Weaving Center on 12/20, which is a Sunday this year, so that one probably belongs to an earlier season's schedule. Check the vendor page before heading out for a particular stall.
The holiday lighting moved to the market's plaza
In its November/December 2025 update, the Village announced a "new location for holiday sing event": the tree lighting would happen Sunday, December 7 at 6 p.m. at the north end of Memorial Plaza, with a synthetic ice rink. The Village's 2025 rink page listed skating from noon to 4 p.m. that day, run by the Pleasantville Parks & Recreation Department.
The rink was a community project. Sponsors included Pace University, Inside Press, Repose Therapy & Wellness, ERA Insite Realty, Beecher Flooks Funeral Home, the Law Office of W. Paul Alvarez, Donna Mueller Photography and Pleasantville Pride. News 12 covered the day under a headline about ice skating and local business deals, describing live music, hot cocoa, photo booths and a rink for skating.
Last year had a gap in the middle. Skating ended at 4 p.m. and the tree lighting started at 6 p.m., which left two hours in between.
2026 runs it as one afternoon
The Village's December 2026 calendar closes that gap. It lists a single "Ice Rink/Community Holiday Lighting Ceremony" on Sunday, December 6, from 2 p.m. to 8 p.m. Last year's noon rink session and 6 p.m. lighting were two separate items. This year they appear as one six-hour block that runs from daylight into dark.
The event listing doesn't yet name a venue, a fee, registration steps or what's included. Last year's event was on Memorial Plaza, but the 2026 location, sponsors and how long the rink stays up are still unannounced, so check the Village calendar before you go.
Six days later, the same calendar lists Breakfast with Frosty on Saturday, December 12, from 9 to 10:30 a.m. It runs during market hours, so a family could come for breakfast and still have plenty of time to shop.
Here is how the plaza-side season lines up, using the market's and the Village's own listings:
| Date | What's happening | Hours |
|---|---|---|
| Sat., Nov. 7 | Market; Living Edge Designs listed for 11/7 | 8:30 a.m. to 1 p.m. |
| Sat., Nov. 14 | Market; Living Edge Designs and Alpacatrax listed for 11/14 | 8:30 a.m. to 1 p.m. |
| Sat., Nov. 21 | Market; Living Edge Designs listed for 11/21 | 8:30 a.m. to 1 p.m. |
| Sun., Dec. 6 | Ice Rink/Community Holiday Lighting Ceremony, venue not yet listed | 2 p.m. to 8 p.m. |
| Sat., Dec. 12 | Breakfast with Frosty, venue not yet listed; market | 9 to 10:30 a.m.; market 8:30 a.m. to 1 p.m. |
| Saturdays through Dec. 26 | Market | 8:30 a.m. to 1 p.m. |
| Saturdays, Jan. through Mar. | Winter market; Six Dutchess Farm weekly | 9:30 a.m. to noon |
Where to warm up near the plaza
Spending the season outside works because there are warm places a few steps away. The Pleasantville Diner shares the market's address, 10 Memorial Plaza, and is open every day from 7 a.m. to 11 p.m. On a Saturday that means it's open before the first market tent goes up and long after the last vendor packs out. A cold 9:30 a.m. market morning in February can end at a booth inside.
The other warm spot nearby is the Jacob Burns Film Center at 364 Manville Road. Its all-ages series this season runs on weekends, so it pairs easily with market mornings and the December events:
- The General, November 7 and 8
- Peter Pan (1953), November 14 and 15
- KPop Demon Hunters sing-along, November 21 and 22
- Frozen sing-along, December 5 and 6, the same weekend as the holiday lighting
- The Nightmare Before Christmas, December 12 and 13, the Breakfast with Frosty weekend
- The Muppet Christmas Carol, December 19 and 20
- Home Alone, December 26 and 27
For adults, the theater's Starring Amy Irving series shows The Competition and Yentl on November 7 and Carried Away and Bossa Nova on December 5, with Q&As on both nights. Both dates fall on market Saturdays. December 5 is also the night before the holiday lighting, which makes it the fullest weekend of the season.
Between the theater and the plaza, look for The Walking Mural in the Jackson Street pedestrian walkway behind the Film Center. Artists Stuart Vance and Gregory Nemec created it, the Pleasantville Public Art Committee started the project, and ArtsWestchester managed it with grant funding through the office of Assemblymember MaryJane Shimsky. It was unveiled in October 2025, according to the Village update. It's a short walk outside between two warm stops.
For more of what has changed downtown this year, see our look at Pleasantville's new storefronts or our Pleasantville neighborhood page.
Our team at Aurora Banaszek keeps a close eye on the village calendar, and we'd be glad to point you to the right Saturday, the right booth or the right film. If you're curious how life around Memorial Plaza connects to a home of your own, schedule a white‑glove consultation.
