
These 9 Towns In Connecticut Were Ranked Among US Favorites In 2025
Some of the small towns in Connecticut were ranked among the US favorites in 2025 due to their appealing connection to the fabric of American history, from when it was one of the original thirteen colonies to the nation’s cultural milestones, as well as the many natural wonders they are close to. In a state that is home to The Hartford Courant, the oldest continuously published newspaper in the US, the New England state of Connecticut has long drawn travelers towards many of these small towns to visit, each of which has character and charisma to appreciate, from the rolling hills of Cornwall to the arts and culture of Washington. With coastal beauty, covered bridges, historic architecture, and lush landscapes, the various towns in Connecticut were ranked among the US favorites in 2025 due to their timeless charm that has defined the state for centuries.
Westport

Thriving along Long Island Sound, Westport encourages newcomers to savor coastal relaxation and cultural vibrancy just an hour from New York City. Its arts scene shines at the Levitt Pavilion for the Performing Arts, where free outdoor concerts and festivals light up summer evenings by the Saugatuck River. When it comes to beachside ambiance, Compo Beach beckons with wide sands, playgrounds, and even remnants of American Revolutionary War cannons. Offshore, Cockenoe Island is a nature preserve perfect for kayaking, camping, or spotting nesting creatures. Likewise, Sherwood Island State Park, Connecticut’s first state park, provides sweeping waterfront views and picnic grounds. Westport’s creative energy is evident in its galleries, theaters, and even its cinematic history, which has served as the backdrop for films and TV shows ranging from The Stepford Wives to Billions. After a day exploring, you can unwind at charming establishments such as the Inn at Longshore in your long weekend or month-long vacation in one of Connecticut’s highly-ranked towns.

Essex

A magnificent homestead along the Connecticut River, Essex is actually three villages—Essex Village, Centerbrook, and Ivoryton—each with its own distinctive charm. In Ivoryton, the historic Ivoryton Playhouse still draws crowds with Broadway-quality performances in an intimate setting. Down by the water, visitors can board the Essex Steam Train & Riverboat, a smooth and serene journey combining rail travel and a river cruise through the scenic Lower Connecticut River Valley. The Preserve, a sprawling coastal forest in Centerbook that is a hotspot for birdwatching and quiet hikes, is within walking distance of the tripartite village. For those craving more time on the water, schooner cruises departing from Essex Village provide a memorable way to explore the river. To complete the experience, you can spend a night at one of the town’s laidback inns, such as the elegant Griswold Inn, which has been welcoming guests since 1776.

Cornwall

Hidden away in the Berkshire foothills, travelers will come across the delightful town of Cornwall, often celebrated as the “greenest town” in Connecticut. Just over 40 miles from Hartford, it is a healthy haven surrounded by miles of woodland trails and untouched scenery, where visitors can explore Wyantenock State Forest, Housatonic Meadows State Park, and Mohawk Mountain State Park. The town is also famed for the West Cornwall Covered Bridge, a red-painted landmark dating back to 1864 that still carries cars across the Housatonic River. Amateur historians will appreciate Cornwall’s connection to Ethan and Ira Allen, the American Revolutionary War figures and founders of Vermont, as well as the homes of Broadway producer Oscar Serlin and humorist James Thurber. After a day outdoors, the cozy Cornwall Inn provides the perfect New England retreat, making this town as inviting as it is picturesque.

Kent

Kent, a former Native American settlement called Scatacook, is a humble and amicable destination in the Litchfield Hills, with an abundant outdoor scenery and a beautiful history to learn about. At the Eric Sloane Museum, you can admire the works and career of prolific author and artist Eric Sloane, whose masterpieces captured the essence of early American life. Elsewhere, the preserved Kent Iron Furnace, a towering remnant of the town’s 19th-century industrial past, intrigues newcomers with its alluring architecture. You should not miss out on a trip through the Kent Falls State Park, where a series of dramatic cascades tumble through the forest, or the chance to hike a stretch of the Appalachian Trail, which winds through Kent on its journey north. For more serenity, Macedonia Brook State Park offers shaded trails, streams, and picnic spots ideal for a slower pace. With its scenic landscapes and compelling heritage sites, Kent promises both adventure and reflection, made even better with accommodations from charming lodgings like the Cooper Creek Inn or The Spirit Horse Farm.
Old Saybrook

Old Saybrook, one of Connecticut’s oldest towns, sits gracefully where the Connecticut River meets Long Island Sound. Its history stretches back to Algonquin-speaking settlements of the Nehantic and Pequot peoples and later as a stronghold of early colonists. Today, certain aspects of Old Saybrook’s past are preserved at the General William Hart House, a stately 18th-century home open to the public with period furnishings and exhibits. For waterfront relaxation, visitors flock to Harvey’s Beach, a family-friendly spot with calm waves and golden sand. Additionally, you can enjoy the tranquil views at Fort Saybrook Monument Park, where interpretive signs recount the town’s early history. Boaters often gravitate toward Saybrook Point Resort & Marina, which offers both luxury cruises and docking for seafarers. Whether for its historic streets or its shoreline beauty, Old Saybrook captures the essence of coastal New England.

Branford

Founded in 1644, Branford has retained its coastal enchantments for centuries amidst New England’s turbulent history. Only about a few minutes from the city of New Haven, it is a convenient and comfortable escape where one can enjoy sampling local flavors. The town’s maritime past can be explored at the Harrison House Museum, a 1724 homestead preserving colonial life. For outdoor recreation, visitors can hike and gallivant in the Stewart B. McKinney National Wildlife Refuge and the Foote Memorial Park. Best of all are boat tours towards the Thimble Islands, a cluster of rocky islets dotted with cottages. Welcoming inns like the Owenego Beach & Tennis Club offer a cozy stay in your humble vacation in one of Connecticut’s favorite and highly-ranked small towns in 2025.

Mystic

Mystic may be small, but its maritime legacy looms large. Once a major shipbuilding center, the town preserves its seafaring history at the Mystic Seaport Museum, where visitors can climb aboard historic vessels, including the Charles W. Morgan, the last surviving wooden whaleship in America. Across the river, the iconic Mystic River Bascule Bridge connects travelers to the bustling downtown and leads to the family-friendly Mystic Aquarium, home to beluga whales, sea lions, and hands-on exhibits. Artists and enthusiasts can explore the Mystic Museum of Art, showcasing local and regional talent. Meanwhile, outdoor adventurers can venture to nearby Mason’s Island for walking trails and coastal views. Whether you are staying at the elegant Whaler’s Inn or the scenic Inn at Mystic, this seaside town is a mystical and magnificent destination for you.

Washington

Within the rolling mounds of Litchfield Hills, the small town of Washington is a refined destination with deep cultural and historical roots. Lake Waramaug shines as an idyllic location for kayaking, fishing, and leisurely walks and picnics. Equally fascinating is the Institute for American Indian Studies (IAIS), which highlights the traditions and history of Connecticut’s Native American peoples through engaging exhibits and a replicated village. The town is also known for its architecture, much of it designed by local architect Ehrick Rossiter. His works, including St. John’s Episcopal Church and the Judea Parish House, give Washington a timeless New England atmosphere. Last but not least is the Smithy Loft Gallery, housed in a former blacksmith shop that now showcases local talent. With luxurious lodgings like the Mayflower Inn & Spa or the Hopkins Inn, Washington is evidently one of the best towns to visit and is favored among many others in Connecticut.

Chester

On the banks of the Connecticut River, the quaint and calming town of Chester showcases the riverine beauty and strong artistic spirit of Connecticut. Shipbuilding and industrial history are best explored in the detailed confines of the Chester Museum at the Mill. Meanwhile, leisurely strolls and tours of the river can be appreciated from the Chester-Hadlyme Ferry, one of the last operating in the state, which leads directly to the whimsical Gillette Castle, a stone mansion resembling a medieval fortress. Art and agriculture are well acquainted at Chakana Sky Alpacas, a small farm where visitors can interact with alpacas and shop for locally made fiber goods. Best of all are scenic and arboreal areas such as Pattaconk Recreation Area, Cedar Lake, and Selden Neck State Park. In a town that combines history, outdoor adventure, and small-town charm, Chester is a quintessential Connecticut getaway that is proud to be one of the many highly ranked towns to visit in the state.
Discover Why These Are the Most Ranked Towns to Visit in Connecticut
From the wooded hills of Cornwall to the sublime shoreline of Old Saybrook, these many towns in Connecticut were ranked among US favorites in 2025 due to their irresistible blend of history, culture, and natural beauty. Some, like Mystic and Essex, celebrate the state’s seafaring past, while others, like Washington and Kent, showcase timeless countryside landscapes and a deep respect for Connecticut’s heritage. Branford and Westport bring coastal fun with modern flair, while Chester charms with its ferry rides and castle vistas. Whether you come for a quiet weekend retreat or a longer adventure, these towns embody the best of New England, inviting visitors to discover for themselves why these towns were highly ranked and favored in the Constitution State.