The Most Beautiful Towns in Connecticut

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Architectural Landmark, Historical Landmark

A tiny town in the Litchfield Hills in Connecticut, Cornwall is famous for having one of the few covered bridges in the area. It’s built from striking red timber in the 19th century, and still serves as an integral part of the town’s infrastructure – as well as being a popular attraction. The town itself features several gingerbread house-like buildings, along with an abundance of trees and greenery, which create a beautiful carpet of reds, oranges and browns during the fall.

Architectural Landmark, Historical Landmark

A classic small New England town, Chester has its roots in shipbuilding and milling, a heritage for which it’s justly proud, and much of this architecture has been carefully preserved. Chester is also notable for its burgeoning cultural scene, with numerous art galleries, boutiques and the local theatre adding to the charming small-town feel. Beyond the main streets lies a beautiful landscape of hills, streams and forests – all accessible by hiking trails from the town.

Architectural Landmark, Historical Landmark

One of the main towns on which Stars Hollow was based in Gilmore Girls, Essex is full of charm, having retained many of its historic buildings. These include a number of farmhouses dating back to before the Revolutionary War, 19th-century Federal-style mansions and the First Baptist Church of Essex – one of only three Egyptian Revival churches built in the United States. The town has a friendly and welcoming community, with a number of inns, shops and galleries. There’s also the Essex Steam Train, an original 19th-century railway and locomotive that tours around the nearby towns.

Architectural Landmark, Historical Landmark

Just 40 minutes by train from central Manhattan, Greenwich is the perfect getaway from the hectic rush of city life and a popular place for commuters in search of a quieter life. The town is comprised of several areas, each filled with historic buildings, charming inns and quaint local museums – all paying homage to the area’s heritage and culture. Thanks in part to its commuter population, Greenwich has more of a cosmopolitan feel than other local towns, with Greenwich Avenue in the center home to brand names and designer boutiques, as well as more quirky independent shops.

Architectural Landmark, Historical Landmark

Known as the top foliage town in the whole of New England, Kent offers a stunning landscape of lush meadows, winding trails and trees decked in green or autumn colors. As well as a charming center featuring antique shops, boutiques and quirky little cafes, Kent is also home to two state parks: Macedonia Brook State Park is a perfect destination for the enthusiastic hiker, with hilltops looking onto the Catskill Mountains; while Kent Falls State Park has an abundance of waterfalls. The quaint town surrounded by gorgeous scenery makes for a perfect New England spot.

Architectural Landmark, Historical Landmark

A perfect blend of wonderful heritage and natural beauty, Milford is a must-visit town in the southern region of Connecticut. Less touristy than some of its cousins, Milford has retained its unspoilt, authentic character, while also boasting various charming spots. The center of the old town has many historical buildings and walks, as well as cafes, boutiques, and booksellers, perfect for browsing and relaxing. Milford has large, peaceful outdoor spaces, including the second-largest green in New England – along with idyllic beaches and seafront walks.

Architectural Landmark, Historical Landmark

Katharine Hepburn’s old stomping ground – the actress lived on the outskirts of the town – Old Saybrook is the perfect waterside New England getaway, with impressive architecture, idyllic natural beauty and friendly locals. The town has many remarkable buildings, from the old-fashioned Saybrook lighthouse to impressive historical manor houses, as well as a soda fountain installed in 1896. A community town, its focal point still lies in Main Street, where numerous independent, family-owned shops vie for attention with original storefronts.

Architectural Landmark, Historical Landmark

Mystic, an attractive town on the New England coast, has a fascinating heritage. Once an important seaport, its history has been wonderfully preserved at the Mystic Seaport – one of the country’s largest maritime museums, with a collection of four historic ships and merchants’ vessels. Walking inland from the impressive port, you’ll come across the charming colonial-period houses of Main Street – and the plethora of delicious seafood restaurants, quaint shops and the Mystic Pizza restaurant, made famous by the 1988 film.

Historical Landmark, Architectural Landmark

Located on the coast just 50mi (80km) north of New York City, Westport has some of the most stunning scenery in Connecticut. The seafront is comprised of a row of beautiful red-brick buildings, the warm colors contrasting with the sparkling blue of the sea. The seafront is particularly striking during sunsets, where the light casts a wonderful warm glow onto the houses and their reflections in the water. Further into the main town, old-fashioned board houses and impressive buildings dating back to colonial times line the streets, interspersed with large, fresh green spaces – perfect for lazy strolls and picnics.

Architectural Landmark, Historical Landmark

Wethersfield has an impressive historical district with over 1000 buildings dating back to 1634, mostly from the 17th, 18th and 19th centuries. The district includes three listed buildings on the National Register of Historic Places, Buttolph-Williams House, Joseph Webb House and Silas Deane house, all outstanding examples of well-preserved colonial architecture. Wethersfield’s abundant natural beauty also sets it apart – the Wethersfield Cove is an idyllic little inlet bordered by lush trees and landscape – with peaceful meadows and narrow winding walks lined with towering trees are dotted around town.