8 Easygoing Small Towns in Connecticut
When you are searching for small-town charm, character, and must-see stops, Connecticut offers plenty to explore. The state’s history as one of the original colonies is visible everywhere, from its white-steepled churches and town greens to picturesque harbors. Because Connecticut is both compact and diverse, it offers an impressive range of experiences within short drives, blending coastal scenery, rolling countryside, and walkable downtowns that are as perfect for quick weekend trips as for longer vacations. From the seaside town of Mystic to the artsy streets of Ridgefield, these eight easygoing small towns invite you to slow down and explore at your own pace.
Mystic
In the southeastern part of the state, the town of Mystic sits on the shores of the Mystic River. As your first stop in town, head to Olde Mistick Village, an open-air village with shops, restaurants, and town events. Opened in 1973, the 1720s-style colonial village is a charming spot, complete with a gazebo and duck pond. While it is a fun spot to visit throughout the year, make a special trip in December for the village’s annual Festival of Lights, where the paths are lit with more than 6,000 luminary candles in decorative bags.
To learn more about the town’s seaside history, plan a trip to the Mystic Seaport Museum, which is the leading maritime museum in the country. With a working shipyard and more than 500 historic watercraft in its collection, the museum is perfect for family members of all ages. With its waterfront location, it is no surprise that the town is home to sea-dwelling animals. See them for yourself by visiting the Mystic Aquarium. There, you can learn more about 300 different species, including African penguins, beluga whales, and sand tiger sharks. Kids will love the museum’s aerial adventure course, where they can climb through the sky across 10 different paths.
Essex
On the Connecticut River, just a few minutes away from the Long Island Sound, you will find the popular sailing destination of Essex. For a historical look at the town, head to Pratt House Museum, a home that housed nine generations of the Pratt family, one of the area’s first known settlers. The home is free and open to the public, and guided tours are available on weekends from June through September. On the grounds, you can also explore the gardens and the home’s reproduction barn, and inside the house, you can see ironwork that is believed to have been forged by Pratt blacksmiths. Continue your historic exploration of Essex at the Connecticut River Museum.
As you walk through the exhibits, you will learn about the history of the region, from the Indigenous people who called it home to 19th-century settlers, and more about the river’s environmental impact. Do you want to work on your golf swing during your trip to Essex? Experienced golfers and novices alike will love visiting the Essex Indoor Golf Center. Its state-of-the-art golf simulators allow you to practice your skills on more than 70 courses from around the world, where you are immersed in hyper-realistic 3D graphics. The center also has a custom bar, The Grumpy Caddy, with a variety of local beers and food to sustain you while you play.
Wethersfield
Less than 10 miles south of Hartford, in the center of the state, is Wethersfield, a quintessential New England town dedicated to preserving its history. At the Webb Deane Stevens Museum, you can learn all about colonial life in the region by exploring three historic homes on-site, including the Joseph Webb House, which served as George Washington’s headquarters in 1781. The museum is open between May and September, with candlelight tours available in December. If you prefer to spend your time in Wethersfield enjoying the great outdoors, head to Mill Woods Park. There is something for just about everyone to enjoy on the park grounds, including an off-leash dog park for your furry friends, a beach and outdoor swimming pond in the summer, a fishing pond, and a lighted softball field and tennis court.
Adjacent to the park, you can also visit the Eleanor Buck Wolf Nature Center, which offers live animal displays and educational exhibits for children of all ages. When you are ready for a delicious meal after a day exploring Wethersfield, check out River: A Waterfront Restaurant and Bar for dinner with a view. Right on the bank of the Connecticut River, the restaurant’s outdoor seating area has 26 heaters to keep you comfortable on cool nights while enjoying dishes like wild mushroom risotto and fish and chips.
Guilford
Located in New Haven County on the Long Island Sound, Guilford has historic sites throughout the town. Explore for yourself by visiting the Henry Whitfield State Museum, which is home to the oldest house in the state, the Henry Whitfield House. Construction of the home began in the 1630s, and it has operated as a museum since 1900. Inside the home, you will find historical furnishings and artifacts, along with scavenger hunt activity sheets to help you spot the most interesting items. The grounds also feature sprawling lawns, a War of 1812-era ship's cannon, exhibit galleries, and a repurposed 1870s barn.
Support a local business when visiting Guilford with a stop at Bishop’s Orchards. The farm has pick-your-own fields from June through October, in addition to a year-round farm market with fresh produce, seasonal pastries, specialty groceries, and cheese from around the world. If you would like to channel your inner artist while in Guilford, make your way to PaperScape Artworks. There, you can explore hand papermaking artist Chris Penry’s galleries, or you can create your own art. There are seasonal workshops throughout the year where you can learn the art of papermaking, or you can schedule studio time on an hourly basis.
Chester
Chester, in the Lower Connecticut River Valley Planning Region, got its start as a mill and shipbuilding town. Today, you can ride the Chester-Hadlyme Ferry into the town or take it across the Connecticut River to the nearby town of Hadlyme. The ferry has been serving locals since 1769, and it is open between April and November, operating on demand as passengers arrive. You can even take your car or bicycle on the ferry, so you have transportation once you arrive. While in town, make time for a stop at the Little House Brewing Company, which operates out of a nearly 200-year-old historic building in downtown Chester. The brewing company has a variety of beers on tap, including non-alcoholic options.
Get to know Chester’s fuzziest residents with a stop at Chakana Sky Alpacas. This sanctuary honors the Indigenous people and animals of the Andean region, with its alpaca and llama farm. On the farm’s website, you can book a visit, where the farmer will take you around, show you the animals, and teach you about life on the farm. It also has a gift shop, where you can purchase hats, scarves, and more made from the soft alpaca fiber.
Ridgefield
In the western part of Connecticut, next to the New York state line, you will find Ridgefield, an artist lover’s paradise in the foothills of the Berkshire Mountains. Plan your visit around a show at the Ridgefield Playhouse, a nonprofit performing arts center that hosts musical performances, stand-up comics, operas, and more. If art museums are more your speed, check out The Aldrich Contemporary Art Museum on Main Street. In addition to its rotating indoor exhibits, the museum features a two-acre sculpture garden. The museum currently has a Third Saturdays program, where admission is free on the third Saturday of every month.
If you would like to catch a movie while in Ridgefield, consider doing so at the Prospector Theater, which supports a great cause. It features four stadium-style movie screens and was constructed to enhance the quality of life for individuals with disabilities by providing meaningful employment opportunities. Approximately 75% of the nonprofit theater’s employees identify as having a disability, and it is committed to providing a range of employment opportunities for individuals with disabilities who wish to work but struggle to find suitable jobs.
East Haddam
When you are looking to explore Connecticut’s great outdoors, plan a trip to East Haddam. Enjoy spectacular waterfall views by visiting Devil’s Hopyard State Park. The park’s most impressive waterfall is Chapman Falls, which drops more than 60 feet down. However, what is most distinctive about the park is the perfectly round potholes in the falls, which range from a few inches to a few feet wide. Another breathtaking spot in East Haddam is Gillette Castle State Park, which features a modern medieval stone castle built in 1914 by William Gillette. The mansion spans 14,000 square feet, and you can purchase tickets to the castle in advance. In addition to Gillette’s home, the state park has hiking trails and picnicking spots for you to enjoy.
Continue your outdoor exploration of East Haddam with a visit to the Ray of Light Farm, an animal rescue and therapy center. The farm is free and open to the public from Thursdays to Sundays, where you can see horses, goats, waterfowl, guinea pigs, and more. You can also book a Wellness Walkabout, where you can enjoy time with a horse handler as you walk along the farm’s Enchanted Trail, groom a horse, and feed some of the animals.
Litchfield
In the northwestern part of the state, Litchfield is a charming town surrounded by rich foliage. Head to Topsmead State Forest in the Litchfield Hills to explore the biking trails, English Tudor-style cottage, formal gardens, and the Orintas Family Butterfly Garden. The forest was once the home of Edith Morton Chase, who left it to the state of Connecticut upon her death, with the goal of preserving it in its natural state of beauty. Learn more about the area’s wildlife by visiting the Ripley Waterfowl Conservancy, an organization dedicated to protecting endangered waterfowl species. It is open to the public between May and November, but you can schedule guided tours by appointment during the offseason.
As you walk around the grounds, you can see swans, chickens, owls, and cranes, and consider packing a lunch to enjoy at one of the many picnic tables around the property. Northwest Connecticut is known for its corn, wheat, and barley, and you can celebrate that with a stop at the Litchfield Distillery. The distillery offers complimentary tours and sample tastings of its spirits, available on a walk-in basis or by pre-booked appointment. If you find a new favorite drink, you can also purchase bottles on-site or order their spirits online, which ship to most states.
Discover Connecticut’s Easygoing Escapes
For anyone looking to explore New England’s hidden gems, these Connecticut small towns offer excitement and adventure. These communities are shaped by their surroundings, whether dense forests, historic buildings, or flowing rivers, inviting you to slow down and enjoy life’s simple pleasures. No matter your preferred travel style, this small but diverse state has something for everyone to love. From exploring state parks in East Haddam to learning about life on the Connecticut River in Essex, memories are waiting to be made in each of these easygoing small towns.
