When I started The CT Beacon, I had no idea how many wineries were tucked away across southeastern Connecticut. What I quickly discovered was that they’re much more than tasting rooms. Throughout the summer, many host outstanding live music, local food trucks, and some of the most relaxing afternoons you’ll find anywhere in the region.
This weekend is a perfect example. I rounded up ten of my favorite winery performances happening Friday through Sunday, giving you plenty of opportunities to sip local wine, discover talented musicians, and spend a few hours enjoying Connecticut’s beautiful countryside.
Brad Bensko at Jonathan Edwards Winery
Friday, July 31 | 5:00 p.m.
Boston singer-songwriter and multi-instrumentalist Brad Bensko brings an evening of Americana, folk, roots, and vintage-inspired pop to Jonathan Edwards Winery. Influenced by the Great American Songbook and the sounds of the 1950s and ’60s, Bensko’s intimate performances pair perfectly with one of southeastern Connecticut’s most beautiful winery settings. Founded in 2001, Jonathan Edwards Winery has become a summer destination for award-winning wines, scenic vineyard views, and outstanding live music, making it an easy choice for a relaxing Friday evening. See Full Details
Peter Mainelli at Kingdom of the Hawk Winery with The Grazing Cart Food Truck
Friday, July 31 | 5:00 p.m.
Kick off the weekend with live music from Peter Mainelli at Kingdom of the Hawk Winery in North Stonington. Pairing acoustic favorites with one of the area’s most scenic vineyard settings, the evening is made even better by The Grazing Cart Food Truck, serving up handcrafted bites while guests enjoy wine by the glass or bottle. Set on a former farm overlooking preserved countryside, Kingdom of the Hawk has become a favorite destination for its contemporary tasting room, relaxing outdoor spaces, and regular lineup of live music that makes summer weekends something to look forward to. See Full Details
Phil Smith at Preston Ridge Vineyard with Rod’s Rolling Roost Food Truck
Friday, July 31 | 5:00 p.m.
Spend your Friday evening overlooking the Connecticut countryside as Phil Smith performs an eclectic mix of classic rock, folk, Americana, country, and modern favorites at Preston Ridge Vineyard. With a song list that spans everyone from Tom Petty and Bruce Springsteen to The Beatles, Pearl Jam, Grateful Dead, and Chris Stapleton, there’s something for nearly every music fan. Rod’s Rolling Roost Food Truck will be on-site serving burgers, cheesesteaks, chicken tenders, fries, and other comfort food while guests enjoy handcrafted wines at the family-owned vineyard, known for its panoramic hilltop views and welcoming atmosphere. See Full Details
Luke & Mike at Stonington Vineyards
Friday, July 31 | 6:00 p.m.
Ease into the weekend with live acoustic music from Luke & Mike at Stonington Vineyards, one of Connecticut’s oldest and most celebrated wineries. The duo provides the perfect backdrop for an evening of locally crafted wines, vineyard views, and summer relaxation. Family-owned since 1987, Stonington Vineyards has earned a reputation for producing award-winning wines and hosting laid-back summer concerts where guests can unwind with friends, bring a picnic, and enjoy one of the region’s most picturesque settings. See Full Details
Sister Funk at Priam Vineyards with The Whey Station Food Truck
Friday, July 31 | 6:00 p.m.
For nearly 20 years, Sister Funk has been entertaining audiences with an energetic blend of rock, country, folk, blues, and pop, sharing stages with artists including Melissa Etheridge, Foreigner, The B-52s, and ZZ Top. Their high-energy show comes to Priam Vineyards alongside The Whey Station Food Truck, known for its creative gourmet grilled cheese sandwiches made with locally baked bread and fresh ingredients. Surrounded by sweeping vineyard views, award-winning wines, and one of Connecticut’s premier winery destinations, it’s an ideal recipe for a memorable summer evening. See Full Details
Mike Ward at Priam Vineyards
Saturday, August 1 | 2:00 p.m.
Spend a relaxing Saturday afternoon with singer-songwriter Mike Ward as he brings heartfelt originals, familiar favorites, and an easygoing acoustic style to Priam Vineyards. Known for his rich vocals, expressive guitar work, and thoughtful songwriting, Ward provides the perfect soundtrack for an afternoon of wine and conversation. Set among rolling vineyards in Colchester, Priam Vineyards is one of Connecticut’s premier wineries, offering award-winning wines, stunning countryside views, and a welcoming atmosphere that makes it an ideal summer getaway. See Full Details
Ben Freiert at Kingdom of the Hawk Vineyard with South County BBQ
Saturday, August 1 | 3:00 p.m.
Enjoy an afternoon of live music, local wine, and authentic barbecue as Ben Freiert performs at Kingdom of the Hawk Vineyard. The Stonington-based singer-songwriter blends indie folk, alternative rock, and Americana into a laid-back acoustic performance that perfectly complements a summer afternoon among the vines. South County BBQ will be serving its slow-smoked specialties throughout the event, while guests can relax with handcrafted wines at one of southeastern Connecticut’s newest winery destinations, known for its modern tasting room and beautiful countryside setting. See Full Details
Dave Sobol at Preston Ridge Vineyard
Sunday, August 2 | 1:00 p.m.
Wrap up the weekend with an afternoon of live acoustic music from Dave Sobol at Preston Ridge Vineyard. Known for his easygoing style and crowd-pleasing mix of classics and contemporary favorites, Sobol provides the perfect soundtrack for a relaxing day among the vines. Family-owned Preston Ridge Vineyard offers handcrafted wines, panoramic hilltop views, and one of eastern Connecticut’s most inviting outdoor settings, making it an ideal place to enjoy a glass of wine and soak in a summer Sunday. See Full Details
Billy Megofna Jr. at Priam Vineyards
Sunday, August 2 | 2:00 p.m.
Spend Sunday afternoon at Priam Vineyards as Billy Megofna Jr. performs an engaging mix of classic rock, folk, Americana, and singer-songwriter favorites. His wide-ranging setlist spans artists including Tom Petty, The Beatles, Neil Young, Jimmy Buffett, The Eagles, Bruce Springsteen, and Zach Bryan, making it easy for everyone to find something familiar. Paired with Priam’s award-winning wines and sweeping vineyard views, it’s the perfect way to slow down, sip a local vintage, and enjoy one of Connecticut’s premier winery destinations. See Full Details
Jason Ingriselli at Saltwater Farm Vineyard with The Rolling Tomato Pizza Truck
Sunday, August 2 | 3:00 p.m.
Close out the weekend with live country music from Jason Ingriselli at Saltwater Farm Vineyard in Stonington. Known for his blend of modern country, Southern rock, and Americana, Ingriselli delivers an energetic performance that pairs perfectly with handcrafted wines and wood-fired pizza from The Rolling Tomato Pizza Truck. Set on the grounds of a beautifully restored former World War II-era airport, Saltwater Farm Vineyard is one of Connecticut’s most distinctive wineries, offering award-winning wines, coastal scenery, and an unforgettable setting for a relaxing Sunday afternoon. See Full Details
