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

Founded in the 1850s as a mill town, Putnam initially produced clothing for Union soldiers during the Civil War. A severe flood in 1955 played a key role in transforming Putnam into a tourist destination, famous for its antique shops and vibrant arts scene. Notable historic landmarks include the 1901 Bradley Playhouse, which remains an active performing arts venue, and the 1874 Putnam Town Hall. Main Street is lively year-round, hosting community events such as International Day in April, the Arts and Crafts Festival in June, and various holiday parades.

Simsbury

Although Hartford is less than a 30-minute drive away, Simsbury feels like a peaceful retreat from city life. Tucked in the Farmington River Valley and encircled by lush hills, Simsbury provides stunning natural vistas throughout the year, especially in fall. Visitors can take in the scenic views from multiple hiking trails, kayaking routes, and bike paths suitable for all skill levels. The town’s Performing Arts Center features the Hartford Symphony in summer, and it is also home to Connecticut's largest tree, the Pinchot Sycamore, with a trunk spanning 26 feet.

Westport

Nestled along the Saugatuck River and Long Island Sound in southwestern Connecticut near the New York border, Westport lies within the state’s renowned "Gold Coast," celebrated for its affluence and scenic beauty. The town boasts a high average annual income and ranks among the top public school systems in the nation. While Westport isn't a typical budget destination, it remains highly attractive. It features four beautiful public beaches, numerous arts and culture venues including the Museum of Contemporary Art, and several nature reserves such as 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!