When Timothy Briere first visited Cassidy Hill Vineyard in Coventry last September, the harvest was underway.
Community volunteers picked grapes alongside the regular crew. A food truck was parked near the log cabin tasting room. Live music drifted across what he calls “rolling meadow fields.”
By the time Briere — the owner of Shelby Supply Co., a Tolland-based metal fabrication and manufacturing business he has run for four decades — walked back to his car, he had made up his mind.
“I felt like, looking towards retirement, I would like to spend my time in something that was enjoyable to me,” Briere said.
He purchased the 137-acre Coventry property in March for $2.82 million.
Across Connecticut, vineyards and wineries have been changing hands at a clip that has caught the attention of industry experts.
At least five Connecticut winery and vineyard properties have been sold since 2024, with more currently on the market, according to CoStar data and public listings.
With dozens of wineries tucked across its hills, shoreline and river valleys, Connecticut has maintained a healthy wine industry for nearly half a century. Now the sector is entering a transition.
Pouring out
Ryan O’Donnell, an attorney at Pullman & Comley whose practice focuses on the hospitality and wine industries, says the recent sales activity reflects a generational handoff.
“What I think is really interesting is not just the volume or the numbers — it’s what is driving the uptick,” O’Donnell said.
The founding generation of Connecticut farm wineries is retiring, he explained, and the next generation often isn’t inclined to take over a labor-intensive, asset-heavy operation.
Hilary Hopkins Criollo, president of the Connecticut Vineyard & Winery Association and owner of Hopkins Vineyard in Warren, sees the same forces at work. Her farm, which has been in the Hopkins family for more than 235 years, was among the first to obtain a Connecticut farm winery permit in 1979, when the state began allowing vineyards to sell wine directly to the public.
“A lot of the wineries are family-owned, and the owners are aging or wanting to retire,” she said. “There hasn’t been the family interest to take it over. I think that’s why some have sold.”
Before 1979, the state’s winemakers could grow grapes and produce wine, but faced restrictions on selling directly to consumers — a barrier rooted in Prohibition-era laws.
A change in state law allowing on-site, direct-to-consumer sales unlocked an industry that, despite the state’s cool climate, does surprisingly well.
Estimates vary on the precise size of the industry. The Connecticut Department of Agriculture in December said there are more than 45 licensed farm wineries in the state, while WineAmerica, an industry association, puts the broader total at about 55 producers. The sector supports roughly 570 acres of vineyards and 7,830 direct jobs, and generates about $1.3 billion in direct economic output, with a broader impact approaching $3 billion when supplier and related activity are included, according to WineAmerica’s latest annual report.
Connecticut has two main grape-growing regions: the Connecticut River Valley and a coastal area warmed by Long Island Sound. Wineries here typically use cold-hardy hybrid grapes — including strains developed at Cornell University and the University of Minnesota — that can survive snowy winters while producing wines with distinctive local flavor, according to Matthieu Wheeler, a winemaker at Cassidy Hill.
New vintage of buyer
What makes the current wave of sales distinctive, O’Donnell argues, is who is doing the buying — and why.
Traditional winery buyers, operators primarily focused on producing and selling wine, have grown cautious as margins have tightened and alcohol consumption has declined.
According to Silicon Valley Bank’s 2026 State of the U.S. Wine Industry report, released in January, consumer spending on wine slid from a pandemic-induced high of $94.4 billion in 2020 to an estimated $74.3 billion in 2025 — a five-year decline of 21.3%.
As a result, O’Donnell said two new buyer profiles are emerging.
The first is what he calls the “lifestyle capital buyer”: someone who has built a successful career, often in business or technology, and wants to own a vineyard as a next chapter rather than a conventional livelihood.
“It becomes a physical asset that, yes, it produces income, and that’s great,” O’Donnell said, “but it also produces an identity.”
The second is the hospitality real estate investor, who sees the vineyard not primarily as a wine production facility, but as a destination — a venue for weddings, corporate events and curated experiences where wine is only part of the fun.
Briere spent 40 years at Shelby Supply and now, in semi-retirement, is channeling his energy into Cassidy Hill’s sprawling campus with 8 acres of planted vines and a tasting room converted from a historic barn.
The previous owners, Bob and Carol Chipkin, built the winery from a cow pasture, opening in 2008. Carol’s death in late 2023 set in motion Bob’s decision to sell and relocate closer to family in Maryland.
More than a few prospective buyers came with development plans in mind.
“We chose to purchase it and continue on with beautiful agricultural land, farm land and vineyard operations,” Briere said.
More than wine
With national wine spending in decline, small wineries that once built their businesses around volume are looking for other ways to fill their glasses.
Criollo, whose Hopkins Vineyard sits in rural northwestern Connecticut, says hosting events has become essential to survive.
“We definitely have a vineyard, we grow our grapes,” she said, “but we need to bring people in. Business has been … challenging for wineries, to be honest.”
At Cassidy Hill, Briere is establishing a full hospitality calendar. The winery has 19 Friday night music events scheduled this season, which can draw close to 200 cars on peak summer evenings.
A stage and outdoor pavilion are under construction near the vines. The tasting room already hosts trivia nights and painting events, and weddings are now on the table. By June, the original homestead on the property is expected to be listed on Airbnb, giving visitors the chance to spend a weekend at a working vineyard.
“In order to sell more wine, you have to host events,” Briere said.
The winery also distributes to more than 30 package stores within about 15 miles of Coventry, and Briere is in talks with a local brewery to bring craft beer to the tasting room.
Cassidy Hill participates in the state-run Connecticut Farm Winery Passport Program, which encourages visitors to travel to different wineries and collect stamps — part of a broader effort to draw more tourism to the industry.
Looking ahead
Connecticut’s wine industry has faced a series of headwinds. Criollo said wineries lost their Sunday-sales exclusivity in 2012 when the state began allowing package stores to open on Sundays, erasing a competitive advantage they long held.
Also, a manufacturer’s permit now allows Connecticut wineries to operate without growing any grapes — instead, they can be imported — which Criollo said has diluted the market for traditional farm wineries.
And a longstanding effort to allow wine to be sold in grocery stores — already permitted in more than 40 states — has stalled repeatedly in the legislature.
“You can go into your grocery store and buy a Connecticut beer, but you can’t buy a Connecticut wine,” Criollo lamented.
Despite those pressures, the state’s winery count has remained relatively stable. The association has added new members even as some older operations have closed or been sold, she said.
Current listings include Chamard Vineyards in Clinton — a 38.75-acre shoreline estate established in 1983, with a French bistro, tasting room and 20 acres of planted vines. The asking price is $8.5 million, according to a listing from Berkshire Hathaway HomeServices.
And in Woodstock, Taylor Brooke Winery & Brewery, a 43-acre operation founded in 1999 by Richard and Linda Auger that includes a winery, brewery, commercial kitchen and residence, is on the market at $3.5 million, according to the listing.
O’Donnell said the industry’s future will depend on whether new buyers bring not just enthusiasm, but a clear understanding of the demands of running a hospitality business and the work required to build an experience that goes beyond wine.
“The idea that you could just sort of take over from your mom and your dad or your grandfather and run it the same way, given all the national trends that you’re seeing in the industry — that’s just not going to work,” he said. “The folks who are really making headway are the ones running this with a much larger hospitality concept, or the lifestyle buyer who has a certain tolerance to price fluctuations that a traditional industry buyer probably wouldn’t have.”
