Labor Day Weekend at Stonington Vineyards
Labor Day Weekend at Stonington Vineyards stretches across three days, September 5–7, with live music, food vendors and wine on the vineyard grounds in Stonington.
The holiday weekend is part of the vineyard’s Summer Pop-Ups series, a collection of casual events designed to add live acoustic music and visiting food vendors to a regular afternoon at the winery. Unlike Stonington Vineyards’ ticketed summer Friday concerts, no tickets are required for the Labor Day weekend pop-ups. Guests can simply visit the vineyard.
Each day gets a different musical act and food vendor. Saturday brings Violet Theory and South County BBQ. James Harris performs Sunday with Jayy’s Food Truck on site. The weekend concludes Monday with Dillon & Nicole and food from the Mystic Lions.
That makes this less a conventional three-day festival than three consecutive afternoons at the vineyard, each with its own music and food.
Saturday: Violet Theory and South County BBQ
Saturday, September 5, starts the weekend with Violet Theory performing from 3 to 6 p.m.
Violet Theory is a familiar name on the southeastern Connecticut and Rhode Island live-music circuit, with a calendar that takes the group through wineries, restaurants, breweries, waterfront venues and other gathering spots across the region.
The group performs in several configurations, including duo and trio arrangements.
For the Stonington Vineyards appearance, the winery is pairing the music with South County BBQ.
Saturday also offers the longest regular vineyard hours of the holiday weekend. Stonington Vineyards’ current summer schedule has the winery open from noon until 7 p.m. Saturdays, leaving plenty of time before and after Violet Theory’s three-hour set.
Guests don’t have to arrive precisely when the music starts. The pop-up is intended to complement an afternoon at the winery rather than operate like a concert with a fixed gate time.
Sunday: James Harris and Jayy’s Food Truck
The pace shifts earlier Sunday, September 6.
James Harris performs from 1:30 to 4:30 p.m., providing three hours of live music during the middle of the winery’s Sunday hours.
Food comes from Jayy’s Food Truck.
Stonington Vineyards is open from noon to 6 p.m. Sunday, giving visitors time on either side of the performance for tastings and wine on the grounds.
It’s also worth knowing that Sunday is one of the days Stonington Vineyards normally offers a complimentary winery tour. Those tours are subject to the winery’s current schedule and conditions, so visitors interested in combining a tour with the Labor Day weekend activities should confirm availability with the vineyard.
Monday: Dillon & Nicole and the Mystic Lions
Stonington Vineyards keeps the weekend going through Labor Day itself.
On Monday, September 7, Dillon & Nicole perform from 1:30 to 4:30 p.m.
The Mystic Lions will handle the food, serving hot dogs, meatball grinders and corn on the cob.
That gives Monday a particularly local character.
The Mystic Lions Club is part of Lions Clubs International’s network of community service organizations, with local Lions projects traditionally supporting charitable and community causes.
The vineyard remains open from noon to 6 p.m. Monday.
With the music ending at 4:30, visitors still have another hour and a half before the winery’s scheduled closing time.
Three Days, Three Different Visits
One useful thing about the Labor Day weekend schedule is that it doesn’t require committing to an entire festival.
There is no three-day pass.
There isn’t a single stage running continuously all weekend.
Instead, Stonington Vineyards has essentially expanded its Summer Pop-Ups concept across the holiday.
Saturday is Violet Theory and South County BBQ.
Sunday is James Harris and Jayy’s.
Monday is Dillon & Nicole and the Mystic Lions.
Someone could choose whichever combination sounds best, or return for more than one afternoon.
And because these are pop-ups rather than ticketed concerts, the vineyard says no tickets are required.
One of Connecticut’s Early Wine-Trail Vineyards
The setting has been part of Connecticut’s modern wine industry for decades.
Stonington Vineyards is a founding member of the Connecticut Wine Trail and sits at 523 Taugwonk Road, away from the busier coastal roads connecting Mystic, Stonington and Westerly.
The vineyard’s proximity to the Atlantic Ocean and Long Island Sound isn’t merely useful for attracting visitors.
It also affects the grapes.
Stonington Vineyards describes its location as having a maritime microclimate shaped by nearby ocean waters, moderating temperatures in a way the winery compares to the conditions found in Bordeaux.
Approximately 6.5 acres are planted with Chardonnay and another 3.5 acres with Cabernet Franc.
The vineyard also emphasizes relatively low yields, cluster thinning and hand harvesting as part of its approach to winemaking.
Chardonnay Has a Particular Place Here
Stonington Vineyards has built much of its reputation around white wine, particularly Chardonnay.
The property’s combination of soils and coastal climate helped shape the varieties planted there, with Chardonnay becoming an important part of the vineyard.
Cabernet Franc provides the primary red grape planting.
The winery’s broader lineup has also included Riesling, rosé and its popular Seaport White blend.
For visitors who want to sample rather than commit immediately to a bottle, regular tastings are part of the experience.
Stonington Vineyards currently prices its standard tasting at $16 per person including tax, with six wine samples and a souvenir glass.
The winery stops tastings approximately 30 minutes before closing.
Bring a Picnic If the Food Truck Isn’t Enough
The visiting food vendors aren’t the only food option.
Stonington Vineyards explicitly allows visitors to bring their own picnic food and snacks.
That’s useful for a holiday weekend when groups may want to settle onto the grounds for several hours rather than simply stop for a tasting.
The winery itself doesn’t operate a full restaurant. It carries smaller food items such as crackers, cheeses, nuts, jams and pretzels, along with flight boxes designed to accompany wine.
Outside food is welcome.
Outside alcohol is not.
Stonington Vineyards’ farm winery and craft café license prohibits guests from bringing other alcoholic beverages onto the property. Anyone bringing a cooler for a picnic should keep it to food and nonalcoholic drinks.
Wine and other beverages licensed for sale by the vineyard are available on site.
Lawn Chairs and a Slower Afternoon
Stonington Vineyards’ outdoor events tend to make use of one of the property’s biggest assets: space.
Rather than treating live music as something that requires everyone to stand in front of a stage, the vineyard’s summer programming encourages the kind of afternoon where people settle in with wine and food.
The property includes lawn space, patios and decks overlooking the vineyard.
For the vineyard’s larger summer concerts, lawn chairs and blankets are explicitly encouraged, and that same relaxed outdoor approach is a natural fit for the smaller Summer Pop-Ups.
The Labor Day weekend schedule also spreads the music through the afternoon rather than pushing it into nighttime.
Saturday’s performance runs 3–6 p.m.
Sunday and Monday run 1:30–4:30 p.m.
It’s daytime wine-country rather than late-night nightlife.
A Labor Day Weekend Alternative to the Coast
The location also provides a contrast with what will be happening a few miles away.
Labor Day weekend is traditionally busy along the southeastern Connecticut and Rhode Island shoreline. Mystic, downtown Westerly and the beaches can all attract holiday crowds.
Stonington Vineyards sits inland on Taugwonk Road, surrounded by the landscape that produces its wines.
The entertainment remains decidedly local: regional musicians, area food vendors and a community organization closing out the weekend on Monday.
There isn’t an elaborate festival itinerary to follow.
Choose an afternoon.
Bring some people.
Find something to eat.
Listen to the band.
And figure out what’s going in the wine glass.
Saturday, September 5
Music: Violet Theory
Music Time: 3–6 p.m.
Food: South County BBQ
Vineyard Hours: Noon–7 p.m.
Admission: No ticket required
Sunday, September 6
Music: James Harris
Music Time: 1:30–4:30 p.m.
Food: Jayy’s Food Truck
Vineyard Hours: Noon–6 p.m.
Admission: No ticket required
Monday, September 7
Music: Dillon & Nicole
Music Time: 1:30–4:30 p.m.
Food: Mystic Lions
Food Menu: Hot dogs, meatball grinders and corn on the cob
Vineyard Hours: Noon–6 p.m.
Admission: No ticket required
Event Details
Event: Labor Day Weekend at Stonington Vineyards
Dates: Saturday, September 5 through Monday, September 7, 2026
Venue: Stonington Vineyards
Address: 523 Taugwonk Road, Stonington, CT 06378
Saturday Hours: Noon–7 p.m.
Sunday Hours: Noon–6 p.m.
Monday Hours: Noon–6 p.m.
Admission: No tickets required for the Summer Pop-Ups
Activities: Wine, live music and visiting food vendors
Outside Food: Picnics and snacks are welcome
Outside Alcohol: Not permitted
Featured image is an artistic representation inspired by the event and may not depict the actual people, location, or activities shown.