Thrift Finds & Vineyard Vibes Pairs a Community Thrift Market With Wine and Live Music

Thrift Finds & Vineyard Vibes Pairs a Community Thrift Market With Wine and Live Music Oct. 3 at Stonington Vineyards, where a three-hour secondhand shopping market gives way to an afternoon of acoustic music, food and wine among the vines.

The Steal My Style Market runs from 1 to 4 p.m. Saturday, followed by an overlapping performance from Mystic singer-songwriter Izzy Malek from 3 to 6 p.m. Food for the afternoon comes from The Grill by Kay.

That overlap between 3 and 4 p.m. should be the sweet spot: thrift vendors still selling, Malek beginning her set, food being served and the vineyard open for wine.

This Is More Closet Sale Than Vintage Show

The thrift market is a little different from the artisan and vintage markets that have become fixtures on the fall calendar.

Steal My Style Market is built around ordinary people opening up their closets and giving their clothes another life. Organizers describe sellers as neighbors, students, parents, teachers, coworkers and other members of the community rather than exclusively professional vintage dealers.

Shoppers can expect a broad mix that may include everyday clothing, designer labels, vintage pieces, current styles, shoes, handbags and accessories.

That also means this isn’t a carefully standardized retail experience. Individual sellers determine what they bring, and the inventory depends on whose closets are represented that afternoon.

For someone who enjoys thrifting, that’s part of the appeal. There is no way to know what might be sitting on the next rack.

The market is open to all ages, and parking is free.

Then Izzy Malek Takes Over the Vineyard

The shopping doesn’t mark the end of the afternoon.

At 3 p.m., Izzy Malek begins a three-hour live set running until 6 p.m., giving market visitors an easy reason to stick around after making their last trip through the racks.

Malek is a Mystic-area singer-songwriter who performs regularly around southeastern Connecticut, with an acoustic sound suited to the vineyard’s outdoor weekend setting.

The timing also creates an hour when the two parts of the event happen simultaneously. From 3 to 4 p.m., visitors can continue shopping while the live music gets underway.

After the thrift vendors wrap at 4, Malek continues for another two hours.

The Grill by Kay Handles the Food

The Grill by Kay will be at the vineyard for the afternoon.

The family-owned food business operates both a mobile food trailer and a kitchen at JD’s Roadhouse in Baltic, along with catering services.

Its mobile menu is known for paninis and comfort-food dishes, giving visitors something considerably more substantial than snacks while spending an afternoon at the vineyard.

The exact menu for Saturday has not been published, so specific dishes shouldn’t be assumed in advance.

Nearly 40 Years of Winemaking in Stonington

The setting adds another dimension to what otherwise might be a simple afternoon thrift market.

Nick and Happy Smith purchased the property that became Stonington Vineyards in 1987, establishing the vineyard on 58 acres in the Stonington Uplands. The winery followed in 1989.

Stonington went on to become one of the founding members of the Connecticut Wine Trail.

Winemaker Mike McAndrew has been associated with the winery since its earliest years, helping establish a wine program particularly known for its Chardonnay and proprietary blends.

Today, the property combines the working vineyard and winery with a tasting room and outdoor areas that regularly host musicians, food vendors and seasonal pop-ups.

On Saturday, the vineyard is scheduled to remain open from noon until 7 p.m., an hour before the thrift market begins and an hour after Malek’s performance ends.

Make an Afternoon of It

This is one of those events where the schedule makes more sense as an afternoon than as a single stop.

Arrive after the market opens at 1 and spend some time going through the clothing and accessories. Grab something from The Grill by Kay. Visit the tasting room or settle outside with wine. At 3, Malek starts playing. The thrift market continues until 4, and the music carries the afternoon through 6.

Wine tastings are currently listed at $16 and include a keepsake glass. The vineyard also offers flights consisting of three 3-ounce pours, although flights are weather-dependent.

Visitors may bring their own food, but outside alcohol is prohibited. Dogs are permitted in the outdoor areas when kept on a leash, but aren’t allowed inside the tasting room or winery buildings.

The combination is pleasantly uncomplicated: hunt through somebody else’s closet, find something you didn’t know you wanted, order some food, pour a glass of Connecticut wine and let the music take over from there.

More information is available at the Event Website link below.

Details

Event: Thrift Finds & Vineyard Vibes
Date: Saturday, Oct. 3, 2026
Location: Stonington Vineyards
Address: 523 Taugwonk Road, Stonington, CT 06378
Vineyard Hours: Noon–7 p.m.
Thrift Market: Steal My Style Market, 1–4 p.m.
Live Music: Izzy Malek, 3–6 p.m.
Food: The Grill by Kay
Market Merchandise: Secondhand clothing, vintage pieces, designer labels, contemporary styles, shoes, handbags and accessories
Ages: All ages
Parking: Free
Wine Tastings: Currently $16 with a keepsake glass
Wine Flights: Three 3-ounce pours; availability is weather-dependent
Outside Food: Permitted
Outside Alcohol: Not permitted
Dogs: Leashed dogs permitted outdoors; not permitted inside the tasting room or winery buildings
Weather: Some activities take place outdoors; check with the vineyard and event organizers for any weather-related changes

Featured image is an artistic representation inspired by the event and may not depict the actual people, location, or activities shown.