Winchester's Busiest Saturday of the Fall: How to Plan October 24, From the Farmers Market to the Haunted House

Winchester has moved Halloween up a week. The Downtown Trick-or-Treat, the Trunk-or-Treat, the first day of window painting and the last night of the Unitarian Society's haunted house all fall on Saturday, October 24. On October 31, the Farmers Market holds its final session of the season on the Town Common.

The two Saturdays need two different plans. The 24th runs from 9 a.m. to 9 p.m. and touches four locations. The 31st is the last chance this year to buy from the market's growers and bakers. What follows covers both days in order, with the times, costs and backup plans a household needs to fit them in.

One Saturday, Twelve Hours

The Winchester Chamber of Commerce, the Family Action Network and the Winchester Recreation Department are co-hosting the Halloween Bash on October 24. Recreation is also running the window painting that afternoon, and Winchester Unitarian Society opens its doors after dark. On a regular market Saturday, the Farmers Market is already on the Town Common from 9 a.m. to 1 p.m.

The Winchester News roundup lists the haunted house's second night as "Saturday, Oct. 23." That's a typo. The town calendar has the second session on October 24, the Saturday.

The Morning: Three Events Overlap

The morning is the hardest part to plan because three events run at the same time. The Downtown Trick-or-Treat starts at 10 a.m., when businesses in Winchester Center open their doors to costumed kids. It ends at 11:30. The Trunk-or-Treat at the Jenks Center lot opens half an hour after the downtown event starts and runs until 12:30. That leaves an hour of overlap, plus the hour after the downtown loop closes. The Farmers Market covers all of it, open from 9 a.m. to 1 p.m. on the Common.

That gives a family with small children a workable order:

1. Get to the market at 9 a.m., before the costumed crowd shows up, and shop first.
2. Walk the downtown storefronts starting at 10 a.m.
3. Head to the Jenks Center lot for the Trunk-or-Treat while it still has an hour or more to run.
4. Go back to the Common for anything you missed before the market closes at 1 p.m.

The Trunk-or-Treat has more going on than the candy. Winchester News lists characters, crafts, balloon twisters and live music. Admission is free for Family Action Network members and $10 per family for everyone else. If it rains, the Trunk-or-Treat moves into Winchester Town Hall. The roundup doesn't give a rain plan for the downtown loop.

Anyone can host a trunk, and it costs nothing. Each host gets free entry and a FAN bag of Halloween treats. To sign up, email [email protected]. For a household that already planned to go, hosting saves the $10 fee and puts the family's car in the middle of the event.

The Afternoon: The Storefronts Get Painted

At 1 p.m., residents start painting Halloween scenes on the outside of designated local business windows using special window paint. Every window needs a Halloween theme. Painters can sign up for Saturday from 1 to 4 p.m. or Sunday from 9 a.m. to 4 p.m. The fee is $35 per window, and registration is capped at 150 participants.

With only 150 spots, the Recreation Department advises registering early through its online portal. Window assignments and instructions go out by email one week before the event.

Saturday's 1 p.m. start gives the morning crowd a lunch break before painting begins. Sunday's longer window lets a family pace itself.

The Evening: 478 Main Street

Winchester Unitarian Society hosts "Dr. Feverdream's Halloween Experiment" for the second year in a row. Organizers describe multi-sensory installations, animatronics, immersive sets, hundreds of props and dozens of actors. One $15 ticket lets visitors choose their path. The Rainforest Adventure is family-friendly. The Dark Path is the intense, mythological route. Concessions and interactive games are open in the Haunted Hall after the walkthroughs. Doors open at 6 p.m. both nights, and tickets are sold through the Unitarian Society's website.

All ages are welcome, from 3 to 93.

Friday, October 23 is the better choice for families who want to keep Saturday for the morning events. That way the haunted house doesn't land at the end of a twelve-hour day.

Lunch and Dinner Between Events

Several Winchester Center restaurants were on the seasonal outdoor dining permit list the Select Board reviewed this spring, according to an April 2026 Winchester News report. Those names are a good starting list for the break between the morning and the afternoon:

• A Tavola, 34 Church St.
• First House Pub, 528 Main St.
• Kyuramen, 538 Main St.
• Frozen Hoagies, 534 Main St.
• Lucia Ristorante, 13 Mount Vernon St.
• Thai Charoen on Main Street, Black Horse Tavern, and China Sky on Converse Place

Nouvelle Maison, at 30 Church St., was also on that permit list. It's running an evening workshop series this fall. A spice-blending session with Curio Spice Co. is on October 14 at 7 p.m.

One more restaurant is coming but isn't open yet. Caffé Ducali, a Filmark Hospitality Group project from restaurateur Phil Frattaroli, plans coffee, breakfast sandwiches, Roman-style pizza and piadini at 959 Main St. Boston Magazine's August 2026 guide lists it as "opening late 2026." The café's own website still says summer 2026, and no firm date has been announced.

October 31: The Market's Last Saturday

With the town's Halloween events finished on the 24th, the market is the main event on the 31st. The Winchester Farmers Market has met on the Town Common since 2008. It runs from the second Saturday in June to the last Saturday in October, 9 a.m. to 1 p.m. This year, the last Saturday in October is Halloween.

The 2026 vendor list is long. It includes Lanni Orchards, Wright-Locke Farm, Flats Mentor Farm, Copicut Farms, Ackermann Maple Syrup, Wilmington Honey Bee, Jax Seafood, OMG Bagels!, Drive-By Pies, Thunder Bread Bakery, Mamadou's Artisan Bakery, Mahalab Bakery, Butternut Bakehouse and Scones by Isobel. In July, Winchester News counted more than 50 vendors, nine of them bakers. The vendor page doesn't say which vendors come on which Saturdays. If you're counting on stocking up from a particular farm or baker before the winter break, check with them directly.

The market has one more special Saturday before Halloween weekend. International Day is October 10, with steel ensemble music, a Chinese lion dance, Rangoli, South Asian dance and music, and tables from local cultural organizations.

November Picks Up Where October Leaves Off

The town calendar slows down after the market closes, but it doesn't stop. Nouvelle Maison has a Cognac-and-Armagnac tasting on November 4 and "The Perfect Board" workshop on November 12, both at 7 p.m. Wright-Locke Farm's free Farm Talk, "Food: Local, Seasonal, Sustainable," is November 17 at 7 p.m. Registration hasn't opened yet. The farm's free Oktoberfest, set for September 27, was canceled because of the expected nor'easter, and no new date had been posted.

November 21 is the next Saturday that packs a lot into one day. The fourth annual Winchester Open Studios runs from 10 a.m. to 5 p.m. at the Jenks Center and, for the first time, Town Hall. The same day, Book Ends hosts an Indie Author Showcase, with local authors signing books from noon to 4 p.m. Like the 24th, it starts in the morning, centers on a few in-town locations and gives a household a full day of plans.

Days like October 24 show Winchester Center at its fullest. If you're thinking about how a calendar like this fits into your plans for the year ahead, Martha Sevigny is happy to talk it through. Schedule a confidential consultation.