10 Connecticut Towns That Are Totally Worth a Visit

If you’re looking for a quick getaway, Connecticut has some hidden gems that are totally worth a visit. From charming coastal towns to scenic spots inland, there’s something for everyone. Whether you’re after great food, unique shops, or just want to take in the scenery, these towns won’t disappoint.

Coastal view of a shoreline with rocks, vegetation, buildings, and a water tower under a cloudy sky. — Image credit: Kailey MarcAurele.

Mystic

A waterfront scene with a mix of red brick and white buildings along the shoreline, featuring a drawbridge partially raised under a bright blue sky with scattered clouds. — Image credit: Kailey MarcAurele.

Mystic is a historic seaport village known for its maritime heritage. Visit the Mystic Seaport Museum, the Mystic Village, Mystic Aquarium, and enjoy a stroll along the picturesque Mystic River. There are also some great restaurants in Mystic, CT.

Chester

A small ivy-covered house with arched windows is surrounded by a lush garden. A white picket fence is in the foreground, and a colorful painting is displayed on an easel near a woodpile. — Image credit: Kailey MarcAurele.

Chester offers a charming Main Street lined with colonial-era buildings, boutique shops, and art galleries. Don’t miss the Goodspeed Opera House, the Chester Museum at the Mill, and Honeycone Craft Ice Cream.

Simsbury

Image of a tall stone tower with a pointed roof, surrounded by a building with a mix of stone and stucco walls under a clear blue sky. Trees partially frame the scene. — Image credit: Kailey MarcAurele.

Simsbury is home to Talcott Mountain State Park, which has a tower you can climb for some stunning views of the surrounding landscape. It’s one of the best trails for hiking near Hartford, CT. Be sure to also visit the Drake Hill Flower Bridge when visiting Simsbury.

Essex

A calm waterfront scene with a wooden dock and pier, a lighthouse structure, and a house on the right, under a cloudy sky. — Image credit: Kailey MarcAurele.

Essex is a quaint town with a rich maritime history. Take a ride on the Essex Steam Train, visit the Connecticut River Museum, and explore the charming downtown area.

Stonington

Stonington is a cute shoreline town with a lot of history. Stonington Borough is very walkable and it has various shops, restaurants, and multiple shoreline public access points. And, there are so many beautiful historic homes to see!

Kent

A cascading waterfall flows over rocky terrain, surrounded by lush green trees in a forest setting. — Image credit: Kailey MarcAurele.

Kent is known for its stunning natural landscapes, including Kent Falls State Park. The town also has a vibrant arts scene with galleries and the Kent Art Association.

Old Saybrook

A white lighthouse stands on a rock breakwater extending into the sea, with waves in the water and a cloudy sky in the background. — Image credit: Kailey MarcAurele.

Old Saybrook is one of the oldest towns in Connecticut, offering beautiful beaches, historic sites like the Katharine Hepburn Cultural Arts Center, and scenic views along the Connecticut River.

South Norwalk

A historic stone lighthouse with a black-domed lantern room sits on a grassy lawn. A pine tree and two people are visible in the background. — Image credit: Kailey MarcAurele.

This town in Fairfield County is on the water has a lot to see and do. Take a ferry out to Sheffield Island to visit Sheffield Island Lighthouse and walk the trails, then grab a bite to eat in the historic downtown.

Canaan

A small waterfall flows over moss-covered rocks in a shaded forest area. — Image credit: Kailey MarcAurele.

Canaan, also known as Falls Village, is a beautiful historic town nestled in the Litchfield Hills in northwestern Connecticut. As the name suggests, this town has waterfalls to enjoy such as Great Falls and Dean’s Ravine. There’s also a cute historic downtown to walk around.

Guilford

A small, red wooden shed stands on a sandy beach with lush green trees in the background under a bright blue sky. — Image credit: Kailey MarcAurele.

Guilford features a picturesque town green surrounded by historic homes and buildings. Visit the Henry Whitfield State Museum and enjoy the scenic views at Jacob’s Beach.