Summer Fun in 2021


We’re excited to hear that many of our favorite summer festivals and events are returning for 2021!

Simon’s Marketplace at Ballek’s Garden Center, Saturdays, All Summer: Chester’s own Simon’s Market has set up shop at Ballek’s Garden Center for the season.

Madison Antiques, Crafts, and Repurposed Good Show on the Green, May 29th.

Holmberg Orchard & Winery Fest, Gales ferry, May 29th, Live music, Holmberg beverages, and a local artisan market.

Chester’s Annual Town-Wide Tag Sale on May 29th, maps available throughout town for this annual hunt.

Chester’s First Fridays, Shop, Stroll and Dine: Openings and drinks throughout town every first Friday of the month.

Arts & Ideas Festival, New Haven,  5/14 – 6/27: Music, theater, dance, workshops and so much more at this annual festival celebrating the spectrum of arts. 

Guilford Art Center presents a Summer Artisan Pop-Up Series: Featuring fine craft artists in an array of media, including ceramics, jewelry, wood, leather, glass, fiber and more!  Pop-up shows will be held on the Guilford Art Center campus on May 29, June 5 and 19, July 10 and 24 and August 7. Saturdays from 10:00am-4:00pm. Admission is free and open to the community.

Mountainside Market at Powder Ridge, Middlefield, Sundays starting 5/30: Local craftsmen and artisans fill this market at Powder Ridge Ski Mountain! 

North Stonington Food Truck Festival, June 5th.

Eastern Connecticut Music Festival, June 5th: Head to the Farm at Carter Hill for this inaugural fest featuring live music, food trucks, artisans, and more.

Goodspeed by the River: The summer-long series offers  musical events under a big tent alongside the iconic Goodspeed Opera House. From rousing classic rock concerts to song-filled evenings with Broadway performers to concert presentations of exciting new musicals, there is something for everyone to enjoy.

High Hopes Big Barn Tailgate featuring Sugar, 6/12/21: This year’s benefit is a gala tailgate with live music, boxed dinners and a lively auction. Get tickets!

Ocean House & Lily Pulitzer, May 29th, 3 – 5pm. Enjoy treats from the Ocean House Food Truck and special discounts at Lily Pultizer in Watch Hill.

Riverfare, Essex, 6/3: A gourmet food and drink tasting even in Essex Village to benefit the CT River Museum

New England Food Truck Fest, North Stonington, 6/5: Food truck festival featuring local favorites!

CT Trails Day, Various Locations, 6/5 & 6/6: Events include hiking, biking, horseback riding, running, trail maintenance, kayaking, educational walks, bird watching, letterboxing, and more for people of all ages and interests. Make sure to register!

CT Open House Day, Statewide, 6/12: Celebrate historic homes, farms, museums and more at free or reduced admission during CT  Open House Day.

Westbrook Marketplace, Westbrook, Opening 6/12 through the rest of the month. Browse this outdoor market featuring local crafters and artisans. 

Eat in the Street, Bank Street New London, first Wednesday of every month through September Celebrating the Summer with Pirates, Bank Street will be closed to traffic, restaurant specials, fireworks, and roaming pirates!

Foxwoods Food Truck Fest, Norwich, 6/12, The Foxwoods Food Truck Festival event is to support and create awareness for the Pancreatic Cancer Action Network & the Special Olympics CT. 

Stonington Vineyards, Summer events include live music and food trucks on Memorial Day Weekend and live music and wine on Father’s Day.

Lyman Allyn’s Spring Soiree on June 12th: “Fly With Me”: drinks, dinner and the art of fly-fishing! To benefit the museum.

Stone Acres Farm begins its summer dinner sessions starting June 15. Make your reservation now!

Shanties & Sails, Essex, 6/15, Geoff Kaufman headlines this Shanties & Sails, with a cruise after on the Onrust after. 

Summer Arts Festival, Essex, 6/19 & 6/20,  A festival elebrating local painters, sculptors, photographers, fabric artists, glass and wood artisans, jewelry designers and crafters and more!

River Jam Festival, Mystic, 6/25 & 6/26, Music fest in Mystic Shipyard! 

Floatchella, Mystic, 6/26, A festive float and paddle around Mystic harbor with live music!

Connecticut Gardens Day at the Flo Gris, Old Lyme, 6/27, Enjoy the Museum’s grounds in full bloom on this special state-wide celebration of historic gardens.

Ivoryton Playhouse opens its summer season with Murder For Two on July 8th.

Niantic Arts & Crafts Show, Niantic, 7/3 – 7/4, Presenting New England’s finest artists and crafters displaying their creations of juried fine arts and crafts including paintings, photography, pottery, jewelry, woodworking and paper products, all on the East Lyme Town Hall grounds.

Essex Auto Club Show, Essex, 7/4, The 12th annual Essex Car Show! Featuring both contemporary and classic models. 

Jonathan Edwards Winery Concert, North Stonington, 7/15, Concert featuring singer-songwriter Donavon Frankenreiter.

Al Fresco Thursdays in Essex Village, Essex, Every Thursday from 7/22 – 9/30, Eat, shop, stroll and socialize in historic Essex Village.

Thursdays on the Dock, Essex, 7/29, A performance by the Little Big Band.

Conquer the Current, Essex, 7/31, A paddleboard regatta finishing by the Connecticut River Museum in Essex Village.

Jonathan Edwards Winery Concert, North Stonington, 8/8, Featuring the band Blues Traveler.

Mystic Outdoor Art Festival, Mystic, 8/14 & 8/15, Showcasing over 200 artists, this festival is a juried, competitive art show. 

Milford Oyster Fest, Milford, 8/21, Over 30,000 oysters all harvested in Milford waters!

The Wooden Boat Show at the Mystic Seaport, Mystic, 8/20 – 8/22, The largest gathering of wooden boats and enthusiasts in New England converge at Mystic Seaport Museum.

Wadsworth Mansion Open Air Market, August 29th: a celebration of food, music and craft.

Live concerts are back at The Kate!