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View from the Gillette Castle terrace in East Haddam, Connecticut.

8 Serene Towns in Connecticut for a Weekend Retreat

The Constitution State of Connecticut has a long and storied history. As one of the original 13 colonies, the state played a crucial role in the American War of Independence. Despite being one of the smallest states in the Union, Connecticut is no slacker when it comes to great places to visit! As a seaport state, it is filled with lighthouses, serene beaches, and beautiful historic architecture that visitors can explore, especially on a weekend retreat. Here are eight serene towns to spend a weekend in bliss!

Mystic

Mystic Seaport.
Mystic Seaport.

This historic seaport town is a truly "mystical" place to visit. First settled in 1654, this underrated Connecticut town proudly displays its history as a safe haven for ships at the Mystic Seaport Museum. This serene town offers many opportunities to explore the high seas, such as with the Argia Mystic Cruises, a traditional sailing ship adventure. The town also hosts the Mystic Aquarium, The Mystic Museum of Art, and a historic steam-powered cider mill built in 1881. For a relaxing retreat, consider visiting Enders Island, an 11-acre center offering walks, gardens, and excellent ocean views.

Granby

Historic building in the district with overgrown vegetation around the driveway
Historic building in the district. Image credit Rachel Rose Boucher via Shutterstock.

Nestled in the Litchfield foothills, Granby is a hidden treasure that offers vineyards, exquisite national forests, and waterfalls. Just over 11,000 people call Granby home, and it has been named the top small town to live in Hartford County. It is home to Tunxis State Forest and Enders State Forest, the latter of which is famous for Enders Falls. Travelers here can also explore a historic village at the Salmon Brook Settlement, which maintains buildings from the 18th and 19th centuries. For places to stay, consider one of the bed and breakfast homes in the area, such as the Truman Gillet House or the O Gawa Shou B&B.

East Haddam

User Gillette Castle State Park, East Haddam, Connecticut.
User Gillette Castle State Park, East Haddam, Connecticut.

Do you have a taste for medieval castles? Then, East Haddam is just the place for you. This small town on the shores of the Connecticut River contains the Gillette Castle State Park, named for a 14,000-square-foot castle built by famed actor William Hooker Gillette in the early 1900s. There is natural beauty everywhere in East Haddam, such as Devil's Hopyard State Park, which features the gorgeous 60-foot waterfall Chapman Falls, and Brainard State Park, a great spot for admiring flowers or birdwatching. You can also see bald eagles near the East Haddam Swing Bridge if you're lucky. For places to stay, consider the Cave Hill Resort!

Branford

Dusk at the Pier, captured during the winter in Stony Creek, Branford, Connecticut.
Dusk at the Pier, captured during the winter in Stony Creek, Branford, Connecticut.

This shoreline town offers many opportunities to relax, recharge, and celebrate. Branford's most picturesque attraction are the Thimble Islands, located just offshore, which provide opportunities for boating, kayaking, fishing, or taking in the scenery. Spend sunbathing or swimming at Branford Point Beach or visit the historic Harrison House Museum, built in 1724. Try out local brews at one of Branford's three breweries, Stony Creek Brewery, Thimble Island Brewery, and Duvig Beer Company. For places to stay, try out one of the marinas in the area, such as Goodsell Point Marina for unique accommodations.

Barkhamsted

Saville Dam with colorful trees in the background, Barkhamsted, CT.
Saville Dam with colorful trees in the background, Barkhamsted, CT.

When it comes to picturesque towns, Barkhamsted is a must-see. Located inside Litchfield County, it is renowned for its unique architecture, such as the Saville Dam, a stone dam built in the shape of a parapet of a medieval castle. The town is a perfect place to get lost in the woods, as a high percentage of it is state forest, such as the People's State Forest and American Legion State Forest. Go fishing on the nearby Farmington River or check out some of the historic buildings on the main street of one of Barkhamsted's two villages: Riverton. There are a few places to stay close to the town, such as Legends on the Farmington, The Old Riverton Inn, and the Royal Coachman Tavern.

Westport

Red brick buildings near Saugatuck River with a bridge close to the downtown in Westport, Connecticut
Red brick buildings near Saugatuck River in Westport, Connecticut. Image credit Miro Vrlik Photography via Shutterstock.

Just over 28,000 people call this small town on Connecticut's "Gold Coast" home. They are truly lucky as Westport offers great charm and things to do. Sherwood Island State Park in the town is a great place to participate in activities on the beach, or you can visit a different island in the area: Hummock Island, which provides tours of the local oyster farm. Learn to sail a boat at the Longshore Sailing School or visit the Smith Richardson Wildlife Preserve to see a diverse coastal forest. Westport's downtown area on the banks of the Saugatuck River has plenty of boutique shops to check out. If you happen to be in town on a Wednesday, you can visit the Westport Astronomical Society at the Rolnick Observatory to stargaze. For places to stay, consider The Inn at Longshore or the Delamar Southport Hotel.

Kent

Bulls Bridge is a covered bridge over the Housatonic River in Kent, Connecticut.
Bulls Bridge is a covered bridge over the Housatonic River in Kent, Connecticut. Image credit: Miro Vrlik Photography via Shutterstock.

This small town of less than 3,000 people, located in the foothills of the Berkshire Mountains, is a hidden gem in the state. The Appalachian Trail runs directly through the town, which makes it great for hikers. Its many trails offer great views of the beautiful Housatonic River, such as Bull's Bridge Recreational Center of St. John's Ledge. One of the most beautiful spots in the town is the Pond Mountain Natural Area, which features a natural glacial lake and mountaintop views. There are plenty of things to check out indoors in the town as well, including the Eric Sloane Museum and Seven Hearths Museum. Kent has two inns, Cornwall Inn and Fife 'n Drum Inn, which are great spots for a weekend getaway.

Litchfield

The historic first congregational church of Litchfield, Connecticut.
The historic first congregational church of Litchfield, Connecticut.

The Litchfield Hills is filled with picturesque towns, and the self-named town of Litchfield is no exception. The town hosts White Flower Farm, a family-owned nursery with tens of acres of beautiful gardens for visitors to walk through and smell the flowers. You can also get a rare view of the mountains by visiting Mount Tom State Park or see a historic cottage at the Topsmead State Forest. The White Memorial Conservation Center provides an outdoor bird sanctuary along with other natural exhibits. With its convenient location, you can explore the rest of the Litchfield Hills while you visit and stay at the colonial-style inn: The Litchfield Inn.

Connecticut has all the perfect elements for a picturesque state, with a long shoreline, forests, historic architecture, and lush wildlife, which create a great combination for a weekend away. From castles to rivers to 18th-century cottages, you can always find something new to explore in the state. Plus, if you feel a bit drained, you can always kick your feet back and sunbathe at the beach. Next time you find yourself in the New England region, consider visiting these eight serene towns in Connecticut.

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