8 of the Most Charming Small Towns to Visit in Connecticut

Connecticut, known as both the Constitution State and the Nutmeg State, is the southernmost state in the New England region. As the third smallest state by size but the fourth most densely populated, Connecticut packs a lot of great little towns into a small area. Some of the towns stretch back to the 1600s, and historic charm abounds no matter where you visit. To help with your travel plans, check out our list of eight of the state’s most charming small towns.

Chester

One of the gems of the lovely Lower Connecticut River Valley, Chester is home to the Chester-Hadlyme Ferry, which has linked communities across the river since 1769. The medieval-style Gillette Castle (1919), now part of a state park, is accessible via the ferry. Back in Chester, Main Street makes a gentle curve through downtown, revealing a row of bustling shops housed in nineteenth century buildings. Walking tour highlights include the Old Town Hall (1793), Federal-style Warner House (1798), and Greek Revival-style Daniels House (1830). Pattaconk Lake and Cedar Lake are great for boating and summertime swimming.

Kent

Set in northwestern Connecticut along both the New York border and the Appalachian Trail, Kent was once an important iron-making town on the Housatonic River. These days, however, Kent is known as a refuge for an eclectic mix of escapees from city life in New York City, especially artists, actors, musicians, and diplomats. As a result, Kent has an amazing collection of antique shops (like RT Facts) and galleries (like Kent Barns) for a one-stoplight town of only 3,000 residents. Kent is also chock-full of fantastic eateries like Ore Hill, Swyft, and Fife ‘N Drum.

Madison

Madison, first settled by colonists in 1641 and later named for Founding Father James Madison, sits at the midpoint of Connecticut's coastline along Long Island Sound. Madison is widely considered to be the state’s best beach town, with summertime tourists flocking to Hammonasset Beach State Park. Downtown Madison still has a classic New England town green, surrounded by bustling bookstores, coffee shops, restaurants, and boutiques. Fans of historic architecture can check out the Grave House (1681), Meigs-Bishop House (1690), Murray House (1690), and more on a walking tour of town.

Mystic

Situated where the Mystic River empties into Fishers Island Sound, Mystic long served as a primary seaport for Connecticut. Today’s Mystic is primarily a tourist destination that continues to honor its seafaring past. The town is home to a premier maritime museum, Mystic Seaport, which houses several preserved sailing ships, including the world’s last intact wooden whaling ship. Mystic also boasts two art museums, a history museum in a 300-year old farmhouse, the Old Lighthouse Museum (in an 1840 stone lighthouse), and Mystic Aquarium. You can also enjoy an evening pleasure cruise on a 1908 steamship.

Old Saybrook

Established in 1635, Old Saybrook more than earns its “old” designation yet is still full of life. From kayaking along the Connecticut River to sunbathing on the two public beaches that front Long Island Sound, Old Saybrook offers a range of outdoor activities. Old Saybrook also has two lighthouses, a classic and busy Main Street that looks like it could be a set from a midcentury Hollywood movie, and a recently refurbished 1901 theater affectionately known as “The Kate.” Fort Saybrook Monument Park is a great place to learn about the area’s history.

Putnam

Putnam was born as a mill town in the 1850s and made clothing for Union soldiers during the Civil War. A devastating 1955 flood helped spur Putnam’s transition into a tourist destination known for its antique shops and lively arts community. The 1901 Bradley Playhouse, still active as a performing arts center, and the 1874 Putnam Town Hall stand as two of many historic architectural highlights. Main Street also hosts fun community events throughout the year, including International Day in April, an Arts and Crafts Festival in June, and several holiday parades.

Simsbury

While it is less than a 30 minute drive to Hartford, Simsbury feels like an escape from city life. Nestled in the Farmington River Valley and surrounded by verdant hillsides, Simsbury offers excellent nature views all year long, but most especially in autumn. You can enjoy the great views from several hiking trails, kayaking runs, and bike trails to suit every skill level. Simsbury’s Performing Arts Center hosts the Hartford Symphony during the summer, and the town also lays claim to the largest tree in Connecticut, the Pinchot Sycamore, with a 26-foot diameter trunk!

Westport

Situated along the Saugatuck River and Long Island Sound in southwestern Connecticut near the New York border, Westport is part of the state’s “Gold Coast” known for its wealth and beauty. The town has a high average annual resident income and one of the highest-ranked public school systems in the United States. Westport certainly is not a budget travel destination, but it is undeniably appealing. The town has four spectacular public beaches, dozens of arts and culture destinations such as the Museum of Contemporary Art, and multiple nature preserves like Sherwood Mill Pond.

We could probably come up with a list of eighty charming small towns in Connecticut, but the eight we have listed here serve as a great starting point for your travels in the Nutmeg State. Compact Connecticut is easy to explore, so make sure to get out there and discover some additional towns to add to your personal “most charming” list. Before you know it, you will be planning your next trip back to Connecticut!