11 Most Underrated Towns In Connecticut
Underrated communities across Connecticut offer forest trails, local art galleries, and seasonal festivals. In the northeast corner, Putnam has built a reputation around antiques, galleries, and a walkable downtown along the Quinebaug River. Chester, tucked near the Connecticut River, revolves around a compact village center known for small theaters, independent shops, and seasonal markets. Farther east, Stonington blends a working harbor with narrow streets and centuries-old homes on a small coastal peninsula. Towns like these show how much character exists beyond Connecticut’s better-known stops.
Putnam
This Quinebaug riverfront town is not only a great spot for canoers and kayakers but delights water sports enthusiasts year-round. Boating, fishing, and even sunbathing on the river bank beaches are popular during the summer months, attracting plenty of traffic from surrounding areas to these pristine shores. However, summer is not the only time for outdoor activities in Putnam.
During winter, residents actively participate in cold-weather events such as the Putnam 5k charity race, which ends with corned beef sandwiches, and offer free craft beer at the Courthouse Bar & Grill for those of legal drinking age. In spring, the community celebrates with the St. Patrick’s Day parade. Putnam warmly welcomes visitors to its museums, restaurants, and the four-story antique store.
Chaplin
Nestled between Hartford, and Providence, off Hwy 6, Chaplin is unique because, while it is one of the few towns established on land that had no previous settlement, it has undergone no significant changes since its incorporation in 1822. That does not mean that the town hasn’t grown. However, with the population hovering around 2,000 dedicated citizens, Chaplin is not in any rush to grow too big too fast.
For those who love fishing but dislike crowded spots, the Natchaug River offers a peaceful retreat. It’s one of the least frequented, yet heavily stocked, fishing locations in the state. While cutting your own Christmas tree is often illegal, at Harmony Farm, you can bring a saw and create a memorable experience selecting and chopping your tree. For authentic maple syrup, visit the Bats of Bedlam Syrup Farm.
Simsbury
Beauty comes alive in this adorable and picturesque town only half an hour outside the capital city. Springtime explodes with color as flowers in every imaginable variety and every inch of the town bloom at once. This even includes the Old Drake Hill Flower Bridge, a walking path overlook that has been a point of community pride for as long as anyone can remember.
However, if you want something a little darker, a little spookier, adventurous visitors enjoy a meal at Abagail’s Grill, a haunting spot where ghosts make a reservation from time to time. Art also has a huge place in the hearts of Simsbury residents, evident in the Simsbury Art Trail, where 37 life-sized sculptures show real-life tasks cast in stunning bronze.
Sharon
On the border of New York in the northwest portion of Connecticut, the hamlet of Sharon and its 2,680 residents welcome you to experience the simpler side of life. From farms that double as art galleries and even an authentic covered bridge, there is much to see and even more to do. Visitors often begin their tour with a stop at the famous Sharon Playhouse.
Enjoy sun and exercise at Housatonic State Park on the shores of the Housatonic River, a terrific spot for camping, swimming, and fishing. Bird enthusiasts will love the Sharon Audubon Center, an entirely enclosed museum complete with a myriad of live birds to capture your wonder. For families and those with a sweet tooth for fresh-grown sugary delights, go pick fruit at the Ellsworth Hill Orchard and Berry Farm.
East Hampton
Famous for the fabrication of bells of all sizes and uses (even bells for toys), East Hampton was a principal export of bells in the 19th century. To this day, bells are still manufactured in the town.
East Hampton boasts many historic landmarks that attract visitors, with Comstock’s Bridge being the most popular. It is the last remaining original covered bridge on the east side of the state and crosses the Salmon River. The bridge is located within the extensive state forests around Lake Pocotopaug, one of Connecticut's largest inland lakes.
Stonington
The final coastal town before entering Rhode Island, Stonington’s appeal largely stems from its closeness to the Atlantic and Long Island Sound. Visitors can find plenty of activities in the downtown area, while local farms and vineyards eagerly welcome new guests. Moreover, the historic Mystic Pizza House gained significant fame even before the movie was shot in the nearby town of Mystic.
No coastal town can be complete without a proper lighthouse, and at the Old Lighthouse Museum, the nature, and history of these important beacons are spelled out in an engaging way, educating all who enter. If the sea is calling, Harbor Cruises are running through the warmer months, as well as Wednesday sailboat races, and trips to DuBois Beach are always a treat.
North Canaan
There are few obsessions more powerful than the love of trains. And while North Canaan no longer makes train parts anymore, the Beckley Furnace Industrial Monument speaks to the forging of iron for train wheels through the better part of the 19th century. Today, it stands very much as it did, preserved, and local historians delight in telling stories about the hallowed days when fires made this important rail car component.
Those who enjoy a cold beer or a glass of wine will appreciate spots like the Land of Nod Winery, Great Falls Brewing Company, and for food and craft beer, the Depot Brew Pub. Afterwards, you can burn off the calories and the drinks with a walk in Campbell Falls State Park, a scenic nature reserve featuring waterfalls that make any walk more romantic.
Kent
It's time to lace up your hiking boots, fill your water bottle, and prepare your camera because adventure calls in Kent. Located in the "Secret Corner," Kent is famous for its stunning fall foliage. Enjoy the scenery as you hike the waterfall staircase trail to Kent Falls, and be sure to take some photos for your social media.
Readers will delight in the House of Books, a charming bookshop on Main Street and home to a treasure trove of literature across every conceivable genre. The industrial age gave us machines that changed the face of our nation and you can see a few marvels of that era at the Connecticut Antique Machinery Association. Then, take a bike tour to Kent Falls Brewing. There is plenty for the entire family to stay entertained no matter what time of year.
Guilford
Restaurants offer various seating options, but have you ever sat on a tree stump? At The Place, you can do so while enjoying lobster caught just off the coast of this charming town on Long Island Sound. Reserve a table for an excellent view of the Fourth of July Fireworks or to watch fishing boats bring in their daily catch.
Boating is a huge part of many local attractions, but that does not cover all the fun and charming aspects of Guilford by a long shot. You can walk the Guilford Green and pop into shops and restaurants, take in an art museum or historical tour, or take a hike through one of the multitudes of parks and wetlands surrounding the town.
Pomfret
A rural environment and historic charm are painstakingly maintained in the middle of the Last Green Valley. One of the oldest incorporated towns in the state, history, tradition, and preserving the scenery is a huge deal to every citizen, with the town government vehement about keeping with the rustic aesthetic.
Even so, it is not a town lost in time. Visitors all year delight in not only the view but an eclectic collection of shops and eateries that have a very loyal following. The winery and distillery run their tours through most of the year to meet the constant demand. With winding country roads, stone walls, and lovely views, coupled with nearby casinos, and theaters, everyone will enjoy the trip.
Chester
Chester's residents march to their own rhythm, embodying a vibrant, creative spirit that they take pride in. The town boasts numerous museums, theaters, and music venues. Yet, what truly draws visitors is its distinctive array of boutique shops and a food scene that promises to delight food enthusiasts.
No trip is complete without a souvenir, and alpaca products might seem unusual, but once you feel their softness, you'll never want sheep wool again. Pick up your own and learn more at the Chakana Sky Alpaca farm. Finish your day with a sunset cruise across the Connecticut River on the Selden III near Gillette Castle State Park.
Big things can come in small packages and Connecticut demonstrates that in all the best ways. Skip New York, New Jersey, and even Massachusetts. Connecticut will capture you in a way that only it can, sharing its wealth of history, offering its vast topography for exploration, and even enticing you into an adventure or romantic trip that you might not have considered before.
