Connecticut’s Favorite Towns for Arts and Culture

The 1,000 Places to See Before You Die travel guide has dubbed Essex “The Perfect Small American Town” and it’s often named among “The 100 Best Small Towns in America”. That’s because Essex offers an ideal blend of history alongside picturesque art galleries, shops, restaurants, and more. Essex is also home to the Connecticut River Artisans, as well as the Cooper & Smith gallery, all well respected for both exhibits and gatherings. You can find events and shows on the Essex Art Association’s website. And don’t miss the chance to take in a show just down the road at the Ivoryton Playhouse, while spending the night at the nearby Copper Beech Inn.

The town of Ridgefield is a destination for art fans, due to the presence of the celebrated Aldrich Contemporary Art Museum. You may not know that you can also visit other arts and sculptures, or take in a performance there too. The West Lane Inn makes a great home base, within walking distance to the Aldrich and the downtown center. See an exhibition at the Ridgefield Guild of Artists gallery. Take in live music, performances, or even a show at the Ridgefield Playhouse or the Ridgefield Theater Barn. And Weir Farm National Historic Site in nearby Wilton is a National Park dedicated to the work of prominent American artists.

The shoreline town of Guilford is home to a popular, and busy, arts community all its own. Take a walking tour of this lovely town. The Guilford Arts Center is a great place to start, where you’ll find a non-profit art school, shop, and gallery filled with treasures. The Guilford Arts Center also hosts the annual Guilford Arts and Crafts Expo on the Guilford Green each July. Browse and shop the local gallery The Bird Nest Salon & Gallery.  

Tucked in along the Connecticut River, just up from where it meets Long Island Sound, the town of Old Lyme has a long history as an artists’ retreat. The Florence Griswold Museum is at the heart of the arts community, with a history as an art colony and the home of American Impressionism. Just next door to the Florence Griswold Museum, you’ll find more art, lectures, and workshops at the Lyme Art Association. Be sure to visit the Lyme Academy of Fine Arts for exhibitions of leading contemporary artists. Then shop for art to bring home at The Cooley Gallery.  Reserve your stay at the cozy Old Lyme Inn and explore all this arts-loving town has to offer—especially during one of the annual arts festivals, like the Old Lyme Arts District’s Midsummer Festival in July.

Just an hour’s ride by train from New York City, the pretty town of New Canaan has a bustling art scene not far from the Connecticut shoreline. From the dramatic appeal of the Philip Johnson Glass House to the art galleries in town, you’ll want to allow for a full weekend to discover all its charms, and include a stay at the historic Roger Sherman Inn. At the award-winning Silvermine Arts Center, explore all kinds of visual arts created by professionals and students alike. The Carriage Barn Arts Center in Waveny Park is a picturesque gallery and performing arts center. And don’t leave New Canaan without a visit to Grace Farms, the striking site that combines arts with mindfulness and wellbeing.