On Saturday, October 24, 2026, Weston has two harvest festivals running from 10 a.m. to 2 p.m. Land's Sake Farm is holding its free Halloween Fall Farm Fest at 90 Wellesley Street. Pumpkin Fest is on the Town Green during the same hours, with every dollar going to Camp Sunshine. Both are planned for the same four hours on the same day, and that tells you more about Weston's fall than either one does alone.
October 24 is the season's hinge. Land's Sake says the end of October closes its full-time farming season. The next day, the Golden Ball Tavern Museum runs a tour of Weston's two oldest cemeteries. From then until Thanksgiving, nearly everything on the town's calendar looks backward: colonial drinking culture, tavern cooking, a World War II battalion, and a trolley park most people have never heard of. The weeks before the 24th are the last of the outdoor harvest. The weeks after belong to local history.
Why the Farm Sets the Date
Land's Sake explains its own timing plainly on the event page:
"The end of October marks the conclusion of the full-time farming season. The days grow shorter, and we have more time to enjoy the seasonal harvest with family and friends!"
So the Farm Fest is an ending as much as a party. The farm brings everything to one place for it. The Up and Covers are playing live music, and there's face painting, temporary tattoos, animal visits and freshly popped popcorn. Frosty's ice cream truck will be parked on site. The farmstand will have in-season produce, pies, fresh bread, other local artisan goods and pumpkins. Costumes are encouraged. You don't need to sign up, and admission is free. Food is for sale.
Pumpkin Fest on the Town Green offers food, games and music, and all proceeds go to Camp Sunshine. Its rain date is Sunday, October 25. That rain date matters, as you'll see below.
Planning the Twenty-Fourth
The two festivals are free to run in parallel because they ask different things of you. At the farm, you stay a while and shop the farmstand. On the Green, you're there for the cause, and your spending supports a charity. With identical hours, you have three realistic plans:
- Farm first, Green second. Get to Land's Sake early for the best of the farmstand pies and bread, then head to the Town Green for lunch and games before 2 p.m.
- Green first, farm second. Start at Pumpkin Fest for the morning games and end at the farm, where the ice cream truck and live music make a natural finish.
- Pick one and stay. With two separate venues running four-hour windows, you can choose based on which crowd your family wants that day.
Weather is the variable. If Pumpkin Fest moves to its Sunday rain date, it will land on the same day as the Golden Ball cemetery tour. Keep an eye on the forecast that Friday.
The Run-Up: A Week of Outdoor Events
The days leading up to October 24 still have outdoor plans, and most of them are about getting to know the town itself.
Saturday, October 17. The Weston Fire Department holds its open house from 10 a.m. to 2 p.m. at 394 Boston Post Road. The Jaws of Life demonstrations run at 11 a.m. and 1 p.m., with a fire extinguisher demonstration at noon. That means three scheduled demonstrations in four hours, so whenever you arrive, you're never more than about an hour from the next one.
Tuesday, October 20. Weston Forest & Trail and the Council on Aging have a walk from 1 to 2:30 p.m. that Weston Media reports the organizers call one "we have not done before." Joel Angiolillo of Weston Forest & Trail leads it through Norumbega Tower Park along the Charles River. Norumbega Park was a popular trolley car park in the late 1800s and early 1900s, when trolleys carried thousands of city residents out for a day in the country. The event listing says the park "is largely forgotten" today. Meet at the four-story tower on Norumbega Road, just south of River Road and north of Maplewood at Weston. Dogs on leash or under voice control are welcome, and there are tailgate refreshments at the tower afterward. Call 781-786-6280 to register.
The Norumbega walk sits right between the two seasons. It's an outdoor fall hike, and the reason to go is the history.
The Day After: Sunday, October 25
The handoff happens fast. The morning after the Farm Fest, the Golden Ball Tavern Museum hosts a tour of Weston's two oldest cemeteries. Pam Fox leads it. She is president of the Weston Historical Society and wrote "Farm Town to Suburb: The History and Architecture of Weston, Massachusetts."
Her book's title sums up the turn the town's calendar makes that weekend. The Saturday celebrates a working farm heading into the end of its full-time season. On Sunday, a historian walks the oldest burial grounds of a town that began as farmland and became a suburb.
Into November: Tavern History and Museum Programs
After the cemetery tour, the calendar moves mostly indoors.
Thursday, October 15, 7 p.m. This one comes before the hinge weekend, but it belongs with the rest of the history programming. Historian and author Brooke Barbier gives a virtual talk for the Golden Ball Tavern Museum on how 18th-century tavern culture and drinking helped fuel the American Revolution, drawn from her book "Cocked and Boozy." Registration is through Eventbrite. Because it's virtual, you can join from your kitchen table.
Saturday, November 7, 11 a.m. The Spellman Museum at 241 Wellesley Street presents "No Mail, Low Morale: The 6888th Postal Directory Battalion in World War II."
Friday, November 13. Food historian Stacy Booth presents "Indian Pudding and Tavern Food" at the Golden Ball Tavern Museum. Coming a few weeks after the farm closes its full-time season, it moves the harvest theme from the field to the 18th-century kitchen.
The Golden Ball's own 2026 calendar shows how deliberate the shift is. It started fall with an outdoor concert on September 10 and its 59th Annual Barn Sale on October 3. After that, it moves to lectures and programs, and then to its "Trimming the Tavern" special exhibit from December 5 through 12.
A Walk With No Date on It
Not everything in a Weston fall needs a calendar entry. The Forbes Conservation Land is a 2.3-acre woodland that the Weston Observer says is nicknamed "the fairy forest." You can reach it on a short walk up Church Street from Weston Town Center, and its paths, bridges and boardwalks follow a stream between entrances on the Rail Trail and on Church and nearby streets.
The land has had real work this year. The Forbes family left it to the town in 1985, with the understanding that the Weston Garden Club would help care for it. Last spring, club members Nancy Bates and Molly Varnau bought plants at the Native Plant Trust and coordinated with Town Conservation Administrator Jordan McCarron. Emily Schadler, the town's conservation stewardship program coordinator, mapped where new highbush blueberry, rough goldenrod, golden alexander, winterberry holly, cardinal flower, wood aster, anise hyssop and black-eyed Susan went in. In June, two Boy Scouts cleared woody invasives, repaired a boardwalk, reclaimed overgrown wetland trails and repainted the entry sign from the Rail Trail. Over the hot summer, McCarron's crew and club volunteers kept the new plants watered.
The timing is good. Wood aster and winterberry holly are both on that planting list, and late October is when a native woodland garden shows what a first growing season produced. The parcel works on either side of the hinge weekend: a short walk the morning before the Farm Fest, or a quiet loop in November after the festivals are over.
Two Practical Notes
The Transfer Station at 195 Church Street is on a temporary schedule. It's open Tuesday, Wednesday, Friday and Saturday from 7 a.m. to 5:30 p.m., with the posted listing running through November 1 "until further notice." If you're planning a post-Halloween cleanout of carved pumpkins and porch decorations, check the town's latest notice after November 1.
Anyone hoping to celebrate the season with dinner on the Town Green will have to wait. The Weston Observer's fall project update on September 4 put the opening target for The Woods at the Josiah Smith Tavern at March 2027. For this fall, the Green's food is whatever Pumpkin Fest serves on October 24.
The shift from harvest to history affects more than weekend plans. For many Weston homeowners, it's also when they start thinking about timing for the year ahead. If you're wondering what this season means for your own property, the Salem Coughlin Team would be glad to talk it through over coffee, with no pressure and no timeline. Request a Confidential Market Valuation and we'll start with what you want to know.
