Walk across the Town Green on a summer evening during a concert and you'll pass the Josiah Smith Tavern the way you have for years: fenced, dark, and quiet. The building has sat at that corner of Boston Post Road since 1757. It has outlived stagecoaches and a Jones family that lived in it for three generations, and the town has discussed its future for roughly fifteen years. The current restaurant proposal includes a parking variance request.
That request concerns a 22-space gap in the current parking plan and requires review by the town's Zoning Board of Appeals. Its current parking plan has a 22-space gap and requires review by the town's Zoning Board of Appeals. The details offer a look at the plans and approvals involved in bringing a restaurant to the historic building.
A Town That's Been Dry Since Prohibition
Weston has no restaurant with a liquor license. It hasn't had one since Prohibition ended in 1933, which puts the current dry stretch at 93 years and counting. If you want a drink here tonight, your options are a package store or membership at one of the town's private country clubs. Brian Piccini, the restaurateur behind the project, put it plainly to NBC10 Boston back in 2024: he moved to Weston in 2018 and quickly realized the town had no public place to have a drink with dinner, and found it ironic that he was "living in a dry town as somebody who runs a hospitality restaurant group."
Celebrate Weston, the town's annual gathering on the Green each May, and summer concerts are among the events held there. The Woods is planned as a restaurant at the Tavern.
The Tavern Has Its Own Older Story
The dry spell and the Tavern's own history are two separate threads, and it's worth untangling them. Josiah Smith bought the land in 1756 and opened his tavern in 1757. It operated as an actual tavern for about eighty years, until roughly 1837, when his son Joel's addition, a Tap Room and a second-floor Ballroom with fireplaces and windows on three sides, had already been standing for decades. After that, the building became a private home for three generations of the Jones family. The Ballroom hosted dances long before it hosted zoning hearings. According to the Friends of the Josiah Smith Tavern's own account of its history, one young woman who attended wrote that "she danced until four o'clock in the morning and never had any lack of partners either." The closing time planned for the revived Tavern will be considerably earlier.
The town restored the building years ago, and the nonprofit Friends of the Josiah Smith Tavern began renting it out as an event space in August 2024. It now also houses the offices of three local nonprofit organizations. The restaurant is the newest chapter, not the first one.
What Piccini Is Actually Building
Piccini isn't new to historic buildings or to Boston's dining scene. His group, Boston Urban Hospitality, also runs Deuxave in Back Bay, Boston Chops in the South End and Downtown Crossing, and dbar in Dorchester. The Woods will be his fifth restaurant.
The concept is a farm-and-sea-to-table menu built around a wood-fired grill, with a stated focus on sustainability and local sourcing. The numbers give a sense of scale: 175 total seats, split between 134 indoor and 41 outdoor seats that are seasonal. There's a planned patio seating 33 that overlooks the Town Green, an interior courtyard seating 16, and three private dining rooms, including a 45-seat space that was once the Tavern's ballroom and another built around the historic bar where, according to Piccini, George Washington himself once stopped for a drink. He's described wanting the menu to stay family-friendly rather than aiming for something precious, in keeping with a building that spent most of its life as somebody's actual house. Piccini has lived in Weston since 2018 and, in the Weston Observer, described the appeal as "how close I can be to the city and yet feel like I'm in nature."
Four Opening Dates and Counting
If you've stopped paying close attention to this project, you're not alone, and the timeline explains why:
- February 2024: NBC10 Boston reported the restaurant was expected to open that October.
- Summer 2024: The state's liquor license, originally granted more than a decade earlier, needed a legislative revision through the Massachusetts Alcoholic Beverages Control Commission. That got resolved in late July, and the Tavern opened as a rentable event space that August.
- May 2025: A Friends of the Josiah Smith Tavern update projected an "early 2026" opening. Piccini appeared at Celebrate Weston that month with new renderings.
- January 2026: Piccini stated a new goal of opening in November 2026, describing the project as entering "our goal to open in November 2026" as it moved into a critical construction phase.
- March 2026: A Weston Observer piece described the restaurant as "slated to open spring 2026."
- Summer 2026: The project hit its current sticking point, a parking variance, which is the subject of ongoing correspondence between Boston Urban Hospitality and the Select Board.
The project has had four stated opening targets over roughly two years. As of this update, November 2026 is the latest stated target.
Parking and the Current Variance Request
The current approval question concerns parking. The Woods does not need further approvals from the Historical Commission or the state liquor board at this point; the Zoning Board of Appeals must consider the parking variance.
| Parking category | Spaces |
|---|---|
| Required under current zoning for a 175-seat occupancy | 77 |
| Provided on-site | 43 |
| On-street spaces already approved by the Planning Board in 2019 | 12 |
| Additional spaces still needed | 22 |
The table summarizes the parking figures behind the variance request. The site can only physically provide 43 spaces on its own lot. Twelve on-street spaces were already approved back in 2019 as part of an earlier site plan. That still leaves a gap of 22 spaces, and the plan on the table is to close that gap through non-exclusive use of additional on-street parking near the property, which requires a variance because Weston's zoning bylaw only counts on-site spaces automatically.
The Select Board sent a letter to the project raising concerns on June 4, 2026. Boston Urban Hospitality responded in detail on July 6, 2026, laying out the case that the combination of on-site parking, the already-approved on-street spaces, and additional nearby on-street parking adds up to a workable solution given the physical constraints of a 269-year-old lot. Notably, the building's septic system and egress have already been reviewed and confirmed sufficient for 175 seats. Parking is the remaining compliance issue to resolve before the project can move from the current paperwork stage to construction.
Where Things Stand This Fall
None of this changes the food, the room, or the reason people are excited about it. The November 2026 opening target depends on the parking variance decision. If the variance moves through the Zoning Board of Appeals this fall, the project can move into final permitting and the remaining construction phase, which the Friends of Josiah Smith Tavern's own updates say includes structural, mechanical, electrical, plumbing, and kitchen-design work still being finalized with the design team. If the variance is delayed, the project may need another opening target.
Either way, the Tavern that has outlasted a Jones family, a Prohibition, and roughly fifteen years of town meetings is closer to serving dinner than it has been at any point in this decade. Residents who want the specifics rather than the rumor can follow the Zoning Board of Appeals agenda directly through the town, or track updates through the Friends of the Josiah Smith Tavern, which has been the most consistent source of hard numbers on this project as it has moved forward.
Whenever the Woods finally opens its doors, it will mark the end of a stretch of Weston history that has quietly shaped how this town spends its evenings. If you're weighing a move here yourself, or thinking about what a place like Weston asks of a buyer and a seller, Michael Quinn is glad to talk through what the town's rhythms, its Town Green, and its long-running local projects actually mean for a home search. Schedule a private consultation whenever you're ready.
This article is general information, not legal, tax or financial advice. Consult a qualified professional about your situation.
