9 Most Welcoming Towns In Connecticut's Countryside
Connecticut, one of America’s original thirteen colonies, contains some of the most welcoming small towns in its verdant and vibrant countryside. Within these heartwarming and accommodating communities, you can immerse yourself in the compelling history of Connecticut, ranging from the publishing legacy of The Hartford Courant, the nation’s longest-running newspaper, to its early colonial roots and the first Thanksgiving, stretching back to 1621. These towns dotted throughout the countryside weave a vivid tapestry of Native American heritage, unique cultural splendor, and amazing natural scenery. Between the forested hills of Cornwall to the relaxing riverbanks in Essex, these destinations reveal the heart and soul of New England.
Cornwall
The tranquil hills of the Berkshire Mountains shelter one of its most endearing towns: Cornwall. Often hailed as Connecticut’s greenest town, Cornwall is just 40 miles northwest of Hartford and thrives as a lush natural retreat into the dense forests and sweeping meadows that have inspired poets like Mark Van Doren. Endless opportunities for exploration abound in places like Housatonic Meadows State Park, Mohawk State Forest, and the nearby Wyantenock State Forest.
A highlight of the town is the historic West Cornwall Covered Bridge, a charming 19th-century structure that spans over the Housatonic River and leads to picturesque countryside vistas. Cornwall’s rustic beauty is matched by its history, as it was once home to Ethan Allen and Ira Allen, key figures in the founding of Vermont. With cozy inns like the Cornwall Inn, the town invites visitors to unwind and experience New England’s natural rhythm in the state of Connecticut.
Kent
Not far from Cornwall, the small town of Kent is an affable and accommodating community with a strong connection to its Native American roots. In the old days, it was once called Scatacook, and it shares much of its surrounding landscapes and natural scenery with its neighbors in the Berkshire Mountains. As you might expect, the area is full of picturesque trails and treks within the bounds of both Macedonia Brook State Park and Kent Falls State Park. The Housatonic River flows through the area, leading you to many opportune areas for fishing and kayaking, as well as giving you access to the nearby Appalachian Trail and Catskill Mountains.
Kent also honors its industrial past with the Kent Iron Furnace, housed within the Eric Sloane Museum, which pays tribute to the prolific writer and artist. The site is listed on the National Register of Historic Places, and is a State Archaeological Preserve. After a day rambling the countryside, you can spend a comfortable night at either The Spirit Horse Farm or Cooper Creek B&B, both of which offer a warm welcome in a quiet, rural setting.
Essex
As one of the most charming and friendly towns along the Connecticut River, Essex is a favorite destination for those looking to escape the big city of New Haven in favor of more peaceful surroundings. Comprised of three quaint villages—Essex Village, Ivoryton, and Centerbrook—each area adds its own character and attractions to the region.
In Essex Village, you can embark on a schooner cruise from the Connecticut River Museum or explore the town steeped in maritime culture. Ivoryton, meanwhile, is known for the Ivoryton Playhouse, a historic theater that stages a wide range of live performances throughout the year. Last but not least, Centerbrook is home to the popular Essex Steam Train & Riverboat, which offers scenic rides into the Connecticut River Valley. For inviting accommodations, the Griswold Inn and Copper Beech Inn offer impressive dining options and the harmonious mix of culture and tranquility that make Essex so appealing.
Old Saybrook
Old Saybrook, perched where the Connecticut River meets Long Island Sound, is not far at all from Essex, but has a vibe all its own. Long ago, this seaside town was once home to the Algonquian-speaking peoples, such as the Nehantic and Pequot. Over time, Old Saybrook evolved into a quintessential New England community, contributing significantly to the region’s colonial development.
Visitors can step back in time at the General William Hart House, a preserved 18th-century home tied to the American Revolutionary War. On the other hand, you can seek relaxation by strolling along the boardwalks of Fort Saybrook Monument Park or dipping your toes in the water at Harvey’s Beach. To refuel after a day spent wandering, head to Old Salt for decadant seafood on the water, and then tuck into Saybrook Point Resort for a night in the lap of luxury.
Mystic
Mystic, a magical little village along the Mystic River, encourages newcomers to seek out its many amazing and memorable attractions in a countryside brimming with natural beauty and wonder. Once a hub for shipbuilding in the 19th century, Mystic's legacy is preserved at the acclaimed Mystic Seaport Museum, home to the Charles W. Morgan, the last wooden whaleship in the world. The Mystic River Bascule Bridge offers iconic and splendid photo opportunities as it lifts to accommodate passing vessels, while, across the river, the Mystic Aquarium introduces visitors to seals, beluga whales, and other marine life in a conservation-centered setting.
Art lovers will definitely appreciate the local works on display at the Mystic Museum of Art. Meanwhile, outdoor enthusiasts can head over to Mason’s Island where various trails and treks await. When the day winds down, you can relax and enjoy a peaceful night at charming inns like Harbor View Landing or The Whaler’s Inn, the latter of which also boasts award-winning restaurant, The Shipwright's Daughter. Between the boats, beaches, and belugas, Mystic will undeniably be a magical small-town experience for everyone.
Washington
In the heart of the Litchfield Hills, the town of Washington offers a quiet, wooded getaway filled with culture and countryside. Set along the Shepaug River in a region teeming with forested hills, this splendid and serene town is beloved for natural attractions such as Lake Waramaug, a favourite destination for fishing, paddling, and lazy lakeside walks. For those interested in the regional heritage of Washington, the Institute for American Indian Studies highlights the traditions of Connecticut’s Indigenous peoples through exhibits and exploratory trails.
Architecture buffs will admire the work of Ehrick Rossiter, whose designs grace many of Washington’s churches, galleries, and civic buildings, including his own personal residence, a sprawling Guilded-Age estate known as The Rocks. To get up close and personal with Washington's historic buildings, accommodations like the Mayflower Inn & Spa and Hopkins Inn offer elegant accommodations and views of the Connecticut countryside.
Chester
On the banks of the Connecticut River just north of Old Saybrook, Chester is a destination where one can take in the charms and attractions of a serene river town. Once home to a bustling mill, its legacy is preserved at the Chester Museum at the Mill, complete with various artifacts and information about rural life in the 19th century. Visitors can cross the Connecticut River aboard the Chester-Hadlyme Ferry, among the country's oldest and one of Connecticut’s last remaining ferries, which leads to Gillette Castle State Park, an enchanting mansion with medieval architecture and stunning river views.
With tranquil getaways like Cedar Lake and the remote trails of Selden Neck State Park nearby, you will feel rejuvenated and relaxed amidst the forests around Chester. For a touch of whimsy, you ought to visit Chakana Sky Alpacas to meet friendly alpacas and learn about sustainable farming. At the end of the day, Chester’s mixture of nature, history, and rustic hospitality makes it a welcoming little town in which to get lost and found in rural Connecticut.
Litchfield
Litchfield, founded in 1721, has captivated newcomers with its range of diverse attractions. Litchfield’s historic heart and town square, for example, centers around the picturesque green, where colonial homes and the iconic First Congregational Church flank the town square. For outdoor lovers, Topsmead State Forest offers over 600 acres of Tudor‑style estate trails and lovely woodland walks. One of the most amazing attractions in Litchfield is the White Memorial Conservation Center, providing access to over 40 miles of scenic trails and a boardwalk over Little Pond and Bantam Lake.
For something with a truly local flavor, Litchfield is also home to the Litchfield Distillery, which offers free tours and tastings of their award-winning spiritis. In spite of its small and unassuming stature, Litchfield more than compensates with its relaxed and rewarding ambiance in a countryside where one is most welcome to try out new and engaging things.
Putnam
The welcoming mill town of Putnam, situated along the picturesque Quinebaug River in Connecticut's scenic Quiet Corner, is a beloved and beautiful destination that many will come to adore. Originally known as Aspinock, Putnam is within walking or biking distance from Roseland Cottage, an 1840s Gothic Revival cottage with photogenic grounds open from June to mid-October.
You can also indulge in a treasure hunt at the legendary Antiques Marketplace, a 22,000‑square‑foot emporium featuring hundreds of dealers, or nearby Jeremiah’s Antiques. Finally, take a stroll or bike ride along the serene Putnam River Trail, which begins at the Arch Street footbridge and weaves through woodlands, old mill sites, and scenic riverbanks. With its mixture of history, art, outdoor adventure, and community spirit, Putnam welcomes you to experience the beauty and serenity of the Constitution State.
Derived from the Algonquian word “Quonehtacut,” meaning “long tidal river,” Connecticut is defined by its connection to land and water, its bridges bound to the past and present. From the pastoral beauty of Cornwall to the boatbuilding history of Mystic, the most welcoming towns in Connecticut’s countryside paint a diverse and captivating picture of New England life. You will be delving into the compelling and enduring Native American cultures in locations such as Washington, chasing waterfalls in Kent, and cruising downriver in Essex. Most of all, you will be having a memorable and merry time in the many beautiful small towns that pepper the state’s countryside. In every corner of Connecticut, these small towns are sure to welcome visitors with open arms full of natural and cultural attractions.
