"It's entirely possible that a Town Green event could also draw patrons who will then use a parking spot for both," Zoning Board of Appeals member Laura Mintz said at the board's September 30 meeting, as the Weston Observer reported. She was talking about The Woods, the restaurant planned for the Josiah Smith Tavern. Her picture of a crowd on the green that walks over for lunch afterward is still at least a season away.
For now the tavern role, as a place where the town meets over food, history and a talk on a weeknight, belongs to the other colonial tavern on Boston Post Road. The Golden Ball Tavern Museum has a fuller fall calendar than the building planned for 175 diners. Trace the gap between the two buildings and you have most of Weston's late October and November.
What Stands Between the Josiah Smith Tavern and Its First Permit
According to the Weston Historical Society, the Josiah Smith Tavern was built in 1757 and enlarged around 1804. It sits in the 300 block of Boston Post Road, which the society calls the town square. Its age is the reason parking became the sticking point. Luke Legere, counsel for the restaurant's operating company, told the ZBA, according to the Weston Observer, that the property is "uniquely constrained due to their shape and configuration and location," and that the constraints trace back to 1757.
Town bylaws require 77 parking spaces for a 175-person restaurant. The Friends of Josiah Smith Tavern explain how the plan gets there: 43 spaces on site, 12 on-street spaces counted earlier, and the 22 additional street spaces the variance now allows. Town Manager Leon Gaumond backed the request. The Observer reported that he told the board he works in the town center about 40 hours a week and that available spots there are "plentiful."
As of the Friends' October 8 update, here is where the restaurant stands:
- Done on September 30. The ZBA unanimously approved the parking variance and also signed off on the special permit for restaurant use.
- Still open. The Select Board, the Friends and Boston Urban Hospitality are working to finalize a sublease amendment. That amendment has to be settled before the operator can apply for a building permit.
- Then construction. The Friends say the operator has finished full construction documents and selected a contractor.
- Later. The restaurant will have to go back to the ZBA for approval of a proposed wooden blade sign.
The concept has been public for a while. Boston Urban Hospitality, led by restaurateur Brian Piccini, is the selected operator. The Friends describe a casual, bright farm-and-sea-to-table restaurant built around a wood-fired grill and seasonal, local ingredients, with the menu still in development. Piccini told the ZBA the plan is lunch from 11 a.m. to 3 p.m. and dinner from 4 p.m. to 9 p.m. Monday through Thursday, with later hours on Friday and Saturday and Sunday brunch starting at 10 a.m. These are planned hours for a dining room that has not been built yet.
October 24, Two Events and No Restaurant
The ZBA's discussion about Town Green crowds gets a real test on Saturday, October 24. From 10 a.m. to 2 p.m., PumpkinFest 2026 takes over the Town Green at 11 Town House Road. The day includes raffles, outdoor games for children, food and pumpkin carving, all raising money for Camp Sunshine, a year-round retreat on Sebago Lake in Casco, Maine, for children with life-threatening illnesses and their families.
Land's Sake holds its Halloween Fall Farm Fest at the same hours on the same Saturday at 90 Wellesley Street. The farm says the end of October marks the conclusion of its full-time farming season, so this is the last big gathering of the farm year. Here is the lineup:
- Live music by The Up & Covers
- Juliana's Pizza Truck, using Land's Sake tomato sauce
- Uhlman's Ice Cream
- A Flower Box Gardens potting shed where visitors pot a flower to take home
- Goats, bunnies, chickens and quail for a meet-and-greet
- Pumpkins, pies and seasonal produce at the farmstand
- A beer garden, which the farm lists as new this year
Entry is free with no registration, costumes are encouraged, and food and drink are for sale.
Land's Sake also has new leadership this season. The Weston Observer reported that Eden Leonard joined as executive director in September. The farm had not posted its late-season farmstand hours or its final open day when we checked, so its own site is the place to confirm those.
The Golden Ball Is Doing What a Tavern Used to Do
The Golden Ball Tavern Museum's history page says Isaac Jones built the tavern on Boston Post Road in 1768. The museum's homepage gives the building period as 1765 to 1768. Its fall program reads like an old tavern's social calendar, with talk, history and a meal as the subject.
Thursday, October 15, 7 p.m. Historian and author Brooke Barbier gives "Cocked and Boozy," a free online lecture on drink and the American Revolution.
Sunday, October 25, 2 p.m. The day after PumpkinFest, the museum and the Weston Historical Society lead a tour of Weston's two oldest cemeteries with Pam Fox, the society's president and author of Farm Town to Suburb: The History and Architecture of Weston, Massachusetts. An introductory talk is followed by the walk, which ends at 3:30, and light refreshments start at 1:45. Isaac Jones links the tour to the tavern. He donated the land for Farmer's Burying Ground and sold 1.5 acres to the town for Central Cemetery, and he and many of his family members are buried in Farmer's Burying Ground. The tour is free, and pre-registration is offered but not required.
Sunday, November 8, 1 to 3 p.m. The museum's events page lists this as the next planned Second Sunday open house, after the October 11 session was cancelled. Ticketed tours also run every Thursday from 10 a.m. to 4 p.m.
Friday, November 13, 6 p.m. Foodways historian Stacy Booth presents "An Ordinary Bill of Fare," a look at the dishes Massachusetts taverns served on the eve of the Revolutionary War. The program is free and held in the museum's Visitors Center, with support from a Massachusetts Cultural Council grant. Space is limited and pre-registration is required.
The November 13 talk overlaps most directly with the Josiah Smith Tavern project. The museum's listing notes that most every colonial town had a tavern where travelers rested and locals gathered for food, drink and news. This November, Weston's version of that evening takes place at a museum, over a presentation about tavern food.
The Rest of the Calendar Through November
The other dates in Weston's fall are mostly within a short walk of these two buildings:
- October 14. A Wings of Fire party at the Weston Public Library.
- October 17, 10 a.m. to 2 p.m. The Weston Fire Department's family open house at Fire Headquarters, 394 Boston Post Road, with demonstrations and children's activities.
- October 17. Storytime and Craft with Jessica Karjanis at the library.
- November 8. Pianist Anthony Ratinov performs at the library, on the same day as the Golden Ball's open house.
- November 23, 7 p.m. A Special Town Meeting.
The Weston Forest and Trail Association has posted its 2026–27 schedule of monthly guided walks, which usually start at 2 p.m. The season opened October 4 at Highland Forest. The association asks walkers to check for last-minute changes before heading out.
The Woods is still aiming for spring. Jay Valenta, president of the Friends of the Josiah Smith Tavern, told the Weston Observer that the project is "still on track, with the significant caveat that the window is closing here to get construction starting this fall." Whether work starts before the cold sets in depends on the sublease amendment and a building permit application, and neither had been completed as of October 8.
At Levy RE Group, we follow changes in Weston's town center as closely as we follow the market, because a restaurant opening on the green affects what a day in Weston looks like. If you'd like to talk about how projects like the Josiah Smith Tavern fit into the town's longer story, contact us. We're glad to share what we know.
This article is general information, not legal, tax or financial advice. Consult a qualified professional about your situation.
