Main Street in Westport, Connecticut. Editorial credit: Miro Vrlik Photography / Shutterstock.com.

8 Most Neighborly Towns In Connecticut

Connecticut, one of the original 13 colonies that broke away from the British Empire, has contributed much to the American Constitution. Both the state and river of Connecticut was based on the Mohegan word “Quonehtacut” which means “long tidal river,” and the most neighborly towns in the state and along the river are replete with historic landmarks and natural sceneries that will dazzle and delight. Between destinations such as Branford and Washington that continue to uphold both the indigenous and modern cultures of Connecticut to towns like Kent and Cornwall that provide innumerable new experiences worth seeing, you will feel a sense of homeliness and ease when immersing yourself in the most neighborly towns in Connecticut this winter and the upcoming spring.

Washington

A colonial-era home in Washington, Connecticut
A colonial-era home in Washington, Connecticut. Editorial credit: LEE SNIDER PHOTO IMAGES / Shutterstock.com

Washington, just 50 miles from the city of Hartford and on the banks of the Shepaug River, is an exhilarating spot to go traipsing through Litchfield Hills and kayaking on Lake Waramaug. Newcomers will be better informed of the Native American inhabitants of Connecticut at the Institute for American Indian Studies (IAIS), and you can also learn to appreciate the architectural masterpieces of Ehrick Rossiter in his historic buildings, the Judea Parish House, the Smithy Loft Gallery, and St. John’s Church among many. More importantly, you can feel rejuvenated and refreshed for a new day of adventure at either the Mayflower Inn & Spa, Windemere Bed & Breakfast, or Hopkins Inn are.

Cornwall

Red building at Railroad Square in Cornwall, Connecticut.
Red building at Railroad Square in Cornwall, Connecticut. Editorial credit: Miro Vrlik Photography / Shutterstock.com.

Travelers can find all manner of exciting and enticing attractions in the small town of Cornwall. Located in the Berkshire Mountains and only about 42 miles from Hartford, Cornwall is considered the “greenest community” in Connecticut as well as the “Home of the Covered Bridge”—specifically the West Cornwall Covered Bridge, built in 1864 and one of the oldest bridges in Connecticut. As local poet Mark Van Doren described Cornwall, “The mind, eager for caresses, lies down at its own risk in Cornwall.” Indeed, you can absolutely lie down and feel caressed in destinations such as the Wyantenock State Forest, Mohawk State Park, and Housatonic Meadows State Park. But if you prefer to be more active, you can always tour the homes of Ethan Allen and Ira Allen, the founders of the state of Vermont, or the homes of author James Thurber and Broadway producer Oscar Serlin. But if your mind does need an actual place to lie down, you can do so in excellent lodgings like the Cornwall Inn.

Essex

The Griswold Inn in Essex, Connecticut
The Griswold Inn in Essex, Connecticut. Image Credit: Joe Mabel via Wikimedia Commons

Around 32 miles west of the city of New Haven, the small town of Essex is one of the best destinations along the Connecticut River and in the Lower Connecticut River Valley Planning Region. As an triumvirate of interconnected communities—Centerbrook, Ivoryton, and Essex Village—Essex welcomes newcomers with a plethora of amenities such as the Ivoryton Playhouse at Ivoryton where local performances enliven the neighborhood. A schooner cruise going across the Connecticut River is accessible to all at the Essex Village, while a vintage train ride, the Essex Steam Train, is available at the demi-town of Centerbrook. Whether you are enjoying bidwatching at The Preserve or resting safe and sound in resplendent lodgings like the Griswold Inn, Safe Harbor Essex Island, or Copper Beech Inn, you will doubtlessly find Essex an excellent vacation retreat in Connecticut.

Kent

Fall colors in Kent Falls State Park in Kent, Connecticut.
Fall colors in Kent Falls State Park in Kent, Connecticut.

Kent, originally known as “Scatacook” by the Native Americans and around 18 minutes from Cornwall, was home to one of Connecticut’s great authors, Eric Sloane. In his time, he wrote 38 books whose origins and inspirations you can learn all about at the Eric Sloane Museum. Other historic landmarks in Kent include the Kent Iron Furnace, which discusses Kent’s industrial growth, and Kent Falls near the Housatonic River which gave the town its name. Additionally, you can fancy scenic treks through te Taconic Mountains and Catskill Mountains via the Macedonia Brook State Park as well as sceneries in Falls Brook and Kent Falls State Park when traversing the Appalachian Trail. If you ever get weary from all your travels throughout Kent, you can always coop up in either the Cooper Creek Bed & Breakfast or The Spirit Horse Farm.

Old Saybrook

Saybrook Point Resort and Marina in Old Saybrook, Connecticut, USA
Saybrook Point Resort and Marina in Old Saybrook, Connecticut, USA. Editorial credit: Rachel Rose Boucher / Shutterstock.com

Approximately nine minutes from Essex, travelers can gain new experiences in the old town of Old Saybrook. The town used to be a settlement of the Algonquin-speaking peoples of the Nehantic and Pequot until immigrants from the Netherlands established a more lasting community in Connecticut’s Gold Coast. Since then, dozens of historic structures have sprouted along the Connecticut River and have retained much of their original structure as seen in the General William Hart House, home to a famous leader in the American Revolutionary War. You can marvel at more of the past at the Fort Saybrook Monument Park, whereas places like Ferry Landing State Park and Harvey’s Beach will soothe your worries away with their natural landscapes. Most of all, accommodations such as Saybrook Point Resort & Marina and the Pier Blue Inn are sure to keep you satisfied and amicable in the neighborly town of Old Saybrook.

Westport

View from road one to Church Lane with Patagonia store and Anthropologie store in Westport, Connecticut.
View from road one to Church Lane with Patagonia store and Anthropologie store in Westport, Connecticut. Editorial credit: Miro Vrlik Photography / Shutterstock.com

Approximately 52 miles away from New York City, the seaside town of Westport enchants visitors with its familiar settings as seen in popular movies and TV shows like Billions, American Housewife, The Sisterhood of the Traveling Pants 2, and The Stepford Wives. With its position on the banks of the Saugatuck River, Westport is a prime destination and getaway from the city bustle if you are eager to see quaint performances at Levitt Paviliion. Furthermore, you can go exploring at Cockenoe Island in Long Island Sound and at the beaches of Sherwood Island State Park. You might also be interested in seeing relics of British cannons left behind in the American Revolution at Compo Beach. There are many more surprises and attractions in store in Westport, even in accommodating establishments such as The Inn at Longshore.

Branford

People enjoying the beach in Branford, Connecticut.
People enjoying the beach in Branford, Connecticut. Editorial credit: Akkulina / Shutterstock.com

Branford is one of the oldest towns in Connecticut ever since New Haven colonists traded “eleven coats of trucking cloth and one coat of English cloth made in the English fashion" to the Mattabesec tribe in 1638. Originally known as Totokett or “Tidal River,” Branford is a six-mile getaway from the city of New Haven and captivates visitors with craft beers from the Thimble Island Brewery, Duvig Beer Company, and Stony Creek Brewery. You can see how the early pioneers and New England inhabitants of Branford used to go about at the Harrison House Museum. Meanwhile, you can go exploring at the Lake Saltonstall Recreational Area, the Stewart B. McKinney National Wildlife Refuge, and Foote Memorial Park. Finally, you can rest up for the evening in establishments like the Owenego Inn or American Inn.

Mystic

Main Street in Mystic, Connecticut.
Main Street in Mystic, Connecticut. Image credit Actium via Shutterstock

There is a town called Mystic on the Mystic River, where blacksmiths, seafarers, builders, and shipwrights gathered in the 19th century to create one of the best port towns in Connecticut. With a history easily discernable at the Mystic Seaport Museum and the last wooden whaleship, the Charles W. Morgan, still in operation in the US, Mystic is truly a mystical town worth visiting. You can traverse the Mystic River Bascule Bridge in order to reach the Mystic Aquarium, where much of the Mystic River’s wildlife are protected and rehabilitated. You might also fancy heading over to the Mystic Museum of Art for the town’s artistic nuances, or traveling the Mason’s Island’s Tree Trails to admire the outdoors. Either way, you ought to at least store your belongings in safe abodes like the Inn at Mystic, The Whaler’s Inn, or Harbor View Landing.

The Takeaway

Connecticut—the site of the first Thanksgiving in the year 1621 and home to the nation's longest-running newspaper, The Hartford Courant—offers a plethora of the most neighborly towns there is that will remind you of a little place called home. From the iconic spots in Westport to Old Saybrook's European-style architecture, outsiders to these neighborly towns will be struck by the attractions and livelihoods of a people that have made a commendable community in one of the original 13 colonies. Discover the state that gave birth to ESPN and Yale University, and enjoy the liberty that Connecticut once fought for against the British Empire, all while exploring its most neighborly small towns.

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