The 10 Friendliest Little Towns In Connecticut
According to the Connecticut State Library, Connecticut can be divided into 169 towns. While friendly faces can be found across them all, some of the warmest welcomes come from the smallest communities, many of which have fewer than 10,000 residents. In the following ten towns, everything from weekly flea markets to annual film festivals brings people together and invites visitors to join in. Beyond the seasonal events, year-round attractions like opera performances, local ice cream shops, and breweries serve as key gathering places for residents in the community. If you are looking to experience Connecticut’s most genuine hospitality, these small towns are a great place to start.
Colebrook
With its annual town fairs, local breweries, and state forests, Colebrook has a laid-back atmosphere where residents always seem to be in a good mood. Travelers can kick off their weekend at Norbrook Farm Brewery, where they will find beer flights, oven-roasted pizzas, and a relaxed outdoor patio. There is even a disc golf course and mountain biking trails on the premises where you can enjoy the outdoors afterward! Residents also frequently head to the Algonquin State Forest for a relaxing afternoon, which is popular for hiking, fishing, and birdwatching. If you will be in town in August, make sure to add the Colebrook Fair to your calendar. This community event features a variety of activities, including a car and motorcycle show, a cardboard boat regatta, and a frog jumping contest.
Canterbury
Canterbury is home to a strong agricultural community, with surrounding farms and restaurants that use locally-sourced ingredients. One great farm to visit is Baldwin Brook Farm, a local dairy farm that offers a closer look at the area's farming culture. Visitors can schedule a tour to learn about the farm's operations and the process behind raw milk production. After exploring the dairy farm, continue your dairy experience in town at the Wicked Cow, a local ice cream shop with over 30 varieties of ice cream! If you enjoy camping, games, and live music, consider attending the annual Easy Does It Fest. During three days in June, this festival features three sets of live music, puzzles and challenges, and campsites for the weekend.
Cornwall
Divided into several quaint, New England-style villages, Cornwall is proud of its heritage and history. One of the ways the town expresses this heritage is through its annual Cornwall Days festival, which takes place each August and features a weekend of music, art shows, a movie night, and lots of food. If you are looking for a welcoming place to grab lunch, stop by the Cornwall Market, which offers freshly baked pastries and bread, sandwiches, soups, and renowned chocolate. The town also takes pride in the West Cornwall Covered Bridge, one of the few remaining covered bridges in Connecticut. For nearly 160 years, it has stood as a symbol of the area's rural heritage.
Washington
Washington is another town in New England that has carefully preserved its history and is eager to share it with guests. One way to experience this heritage is through the Washington Green Historic District, which dates back to the 18th century and reflects the town’s evolution from a colonial village to a modern community, with architectural styles ranging from Colonial and Federal to Gothic Revival. After strolling through some of Washington’s historic landmarks, hungry travelers can grab a bite at The Po Cafe, a beloved cafe and bakery that serves fresh fruit poptarts, oversized cookies, coffee, seasonal drinks, breakfast dishes, and sandwiches. Each fall, the community comes together for the annual Harvest Festival, which features a variety of seasonal activities like pumpkin carving, a hay maze, train rides, live music, and more.
Mystic
Throughout the year, the community of Mystic hosts some of the quirkiest and most interesting festivals in the state. Each February, the community comes out of hibernation for the annual Charity Chowder Cookoff and Cabin Fever Festival, in which many local restaurants from around the region serve their version of the famous New England dish. In July, travelers can attend the Antique & Classic Boat Rendezvous & Parade, in which boats from around the country gather, featuring incredible examples of sailboats, runabouts, and cruisers. For even more maritime culture and history, stop by the Mystic Seaport Museum, which showcases a recreated 19th-century seafaring village, a planetarium, and various historical and art exhibitions.
Kent
Kent welcomes travelers with an eclectic mix of shops and restaurants, many of which are locally owned and operated. Terston is a great shop to check out during your visit. It is a chic boutique that sells clothing, candles, dishware, perfume, and more. For a hearty meal, there are plenty of restaurants and taverns to choose from, such as Kingsley Tavern, which serves a varied menu consisting of sandwiches, salmon, fish tacos, soups, and pastas. The annual Kent Holiday Fest always attracts a crowd, ringing in the holiday spirit with activities like a parade of lights, festive crafts, hot chocolate, and storytimes for the kids.
Sharon
Located in northwestern Connecticut, near the border with New York, travelers will find Sharon to be a relaxed community with plenty of community spaces. The Hotchkiss Library is well worth a visit while in town. Dating back to 1893, its iconic stone facade remains a landmark, and the library continues to serve the community to this day. Those in need of some fresh food and produce can visit the Sharon Farm Market, which features locally-sourced ingredients brought in by local producers every day. Each summer, Sharon’s Parks and Recreation department hosts the annual Arts & Crafts Fair, which has been a town tradition since 1958, featuring juried art exhibitors on the town green.
Ridgefield
Founded over three hundred years ago, Ridgefield has centuries of culture and heritage to explore. The Keeler Tavern Museum & History Center is an excellent place to begin your tour, preserving centuries of local and national history, as well as offering educational and cultural programs to connect with the community. Those interested in contemporary art should plan a visit to the Aldrich Contemporary Art Museum, home to a sculpture garden and an interesting lineup of rotating exhibitions. This May, Ridgefield hosted its 10th annual Ridgefield Independent Film Festival, which featured a screening of over 30 independent films.
East Haddam
With its farmers markets, local opera company, and family-owned restaurants, East Haddam proudly supports and celebrates its local community. From June through September, local vendors come together each Wednesday for the weekly East Haddam Farmers' Market, in which visitors can shop for local produce, food products, and crafts. For some fine American cuisine, the Gelston House is the place to go, offering guests incredible views of the Connecticut River. It is also right next door to the Goodspeed Opera House! Upcoming shows at the opera company include Ragtime, All Shook Up, and A Chorus Line.
Woodbury
As the “Antiques Capital of Connecticut,” visitors will find plenty of welcoming antique stores throughout Woodbury. Travelers can start their antiquing expedition at The Hidden Acorn, a highly rated antique store that offers a variety of vintage products, from antique furniture to restored goods. If you are searching for a more upscale vintage item, consider stopping by Mill House Antiques & Gardens, which has been operating in the community since 1964, offering well-preserved and fine antique items. Travelers who will be visiting Woodbury on the weekend, meanwhile, can pop into the weekly Woodbury Antiques & Flea Market, which offers free admission and has been a beloved tradition in town for decades!
Connecticut as a whole tends to have a more laid-back feel than many of its fast-paced neighbors in the Northeast. However, a few towns stand out for their exceptional friendliness, offering full calendars of cultural festivals, local art museums, and family-owned restaurants with locally sourced ingredients. Regardless of how you like to spend your vacations, these ten towns offer experiences that are as welcoming as the people who live there.
