Downtown Milford, CT

11 Most Beautiful Small Towns In Connecticut

The magnificent state has been known since pre-Columbian times, now reminiscent in the historical sites throughout, in the surroundings of spectacular natural scenery. These small towns make Connecticut feel like a poem, beautiful to the tears.

waterfall with church in background in the center of Milford, Connecticut.

A picturesque blend of history and natural beauty of southern Connecticut, Milford is a must-visit, less touristy destination for the unspoiled environment and authentic character. The laid-back beach town offers to experience the natural charm of authentic New England with many quirky shops and good eats. Boasting various charming spots, one will find many historical buildings, cafes, boutiques, and book vendors in the center of the old town along the streets dissected by narrow picturesque passages. The immense scenic surroundings offer a peaceful time spent with the second-largest green space in New England and the idyllic beaches with seafront walks. For attractions, there is a myriad of water recreation opportunities and multiple memorials giving a nod to the town's rich history.


Seth Seelye House in Bethel, Now a Public Library, Photo by By Doug Kerr
Seth Seelye House in Bethel, Now a Public Library, Photo by By Doug Kerr

Despite being home to big companies like PT Barnum, Meg Ryan, and Duracell, the economically-thriving town of Bethel is also full of natural beauty. A mere hop from New York City immerses one into the quaintest setting with a tiny center full of boutiques, antique stores, and the best farm-to-table eateries. Settled way back in 1650, there are countless historical sights and buildings, with the oldest on the Main Street dating to the 1700s. Surrounded by ripe beauty, one will want to venture out for day-long farm visits and picnics, among other outdoor adventures. There are also hiking trails, mountain biking paths, and sailing lessons, after which one will feel compelled to down an enormous milkshake at the local favorite Cream and Sugar. The in-town indie movie theater is great for an atmospheric flick in the evening, while come at the right time, and one will be at the mercy of the Connecticut Film Festival.


winter festival
Winter festival in Chester, Connecticut

The welcoming oasis of Chester is a historic rural town settled in 1692 on the scenic hillside of the Connecticut River that was long-inhabited before Europeans landed on the continent. Set within marinas, lakes, and brooks, this town has endless waters to pursue, while the thousands of state forest acres are dotted with breathtaking waterfalls to hunt for. The former shipbuilding and mill town that are reminiscent of the past but not stuck in it are filled with classic-feel attractions like art galleries and the Norma Terris Theater second stage of the world-renowned Goodspeed Opera House. It is a true godsend for the artists who seek inspiration and a wholesome-feel vacation spot with lovely sights. The active will enjoy days of hiking, cycling, and camping at the Cockaponset State Forest or the Selden Neck State Park. Back in town, historic architecture, including the magnificent Gillette Castle, await.


The Housatonic River in Cornwall, Connecticut

Bordered by the Housatonic River in the foothills of the Berkshire mountains, Cornwall is a real country gem of immense natural beauty that one must experience to believe. Commonly known as the greenest town in the state, it is a perfect cleansing getaway for the lungs, away from the city fumes back home. The variety of beautiful landscapes to hike, bike, and fish range from the gorgeous Mohawk State forest to the sunny countryside set on the rolling hills. Complete with modern amenities and recreational choices, the streets of Cornville are full of historical aura, including ancient architecture and one of the only three surviving old covered bridges in the state. One must revisit the town in winter when the snow-sports enthusiasts start trickling in for its most popular attraction, the Mohawk Mountain Ski Area.


Connecticut river Essex
Connecticut River in Essex, Connecticut

The Gilmore Girls fans will instantly recognize the beautiful town as one of the main settings in which Stars Hollow was based. Full of historic charm with many old buildings, Essex emanates a sense of tranquility reminiscent of the slower days of the past. Surrounded by numerous farmhouses dating back to before the Revolutionary War, this town allows one to have endless field trips to see these 19th-century Federal-style mansions. Amongst them, the magnificent First Baptist Church of Essex is one of the only three Egyptian Revival churches that were built in the nation. Despite its old-timey feel, the town boasts modern attractions, including welcoming accommodations, various shops, and galleries to peruse. The Essex Steam Train is an original 19th-century railway locomotive that will take one to the nearby towns and for more impressive sights of the region's scenically rich offerings.


A Sailboat in Greenwich, Connecticut

Forty minutes away by train from central Manhattan is the small town of Greenwich comes with big recreational opportunities. Greenwich is divided into several areas, known among the commuters who like to get away from the hectic rush into the quieter life. Regardless of where one lands, the area will be full of historic buildings, charming inns, and quaint local museums to explore. The vibrant downtown streets are lined with endless shopping outlets and many restaurants to stroll endlessly about and peruse. The Greenwich Historical Society offers to impart intriguing knowledge about how the early settlers came about to Connecticut, as well as a park and cafe on the grounds. Retaining the cosmopolitan feel on Greenwich Avenue with brand names and designer boutiques, the town also pays homage to the area's heritage and culture, including independent shops, local art galleries, and historical sights.


Macedonia State Falls in Kent, Connecticut

Although renowned in the New England region as the top town to visit when leaves start turning color, it is just as imperative to experience Kent during summer for the freshest-air walks within the vividly green foliage. The scenic town comes with a stunning varying landscape of lush meadows, hilltops looking onto the Catskill Mountains, and the Kent Falls State Park full of waterfalls. In-town, one will be greeted by a charming center full of antique shops, boutiques, and quirky terraced cafes surrounded by more scenery. There's also the Macedonia Brook State Park, where one will find endless hiking opportunities along the wooded paths with more awe-inspiring falls. Bulls Bridge in Kent is one of the few remaining 19th-century covered bridges, marking the historic site where George Washington crossed the river in 1781.


Madison, Connecticut

The stunning small town set 30 minutes from New Haven is bountiful in nature and history. Madison's streets come with beautiful historic homes, shops, and atmospheric cafes. The independent bookstore RJ Julia is a must-visit for the literature fans, while the Madison Beach Hotel, operated by Hilton and set overlooking the Long Island Sound, calls out to the romantics. The next-door neighbor, Hammonasett Beach State Park's beautiful natural world, is a known camping trip destination with endless water pursuits. The Surf Club Beach, East Wharf, and West Wharf beaches come with unique vibes to attract fishers, surfers, and picnickers. After a day-full out enjoying Madison's beaches and the scenery around, the town awaits with a waterside restaurant galore and vibrant nightlife.


Mystic Seaport in Mystic, Connecticut

Set on the New England coast, Mystic stands behind its name as an attractive town with a fascinating history. A former significant seaport of the region, one can discover its wonderfully preserved heritage at the majestic Mystic Seaport. One of the country's largest maritime museums, it is home to four historic ships and merchants' vessels. The Main Street brims with charming houses standing there from colonial times, interspaced by countless delicious seafood eateries, quaint shops, and the world-renowned Mystic Pizza restaurant. The town made famous by the 1988 film continues to attract fans with its archetypal New England vibe and laid-back tourist attractions as a magically tranquil getaway.  

Old Saybrook

A Lighthouse by the Sea in Old Saybrook, Connecticut

Old Saybrook was settled four centuries ago by a Dutch colony and later Anglicized to bear vestiges of both European cultures and its own town seal. With its idyllic natural beauty, including beautiful beaches, the town was also made famous by the ageless actress Katharine Hepburn, who lived on the outskirts but surely visited Old Saybrook. The vibrant downtown boasts impressive architecture and a small wander-worthy main street that packs-in numerous independent, family-owned shops with original storefronts, cafes, and restaurants great for people-watching. The many remarkable buildings include the old-fashioned Saybrook lighthouse, a soda fountain from 1896, the famous Black Horse Tavern, and the Connecticut Valley Railroad and Turntable Site.


Westport, Connecticut

The small coastal town of Westport is only 50mi (80km) north of New York City for a quick getaway into some of the most stunning scenery in Connecticut. The picture-perfect facade aligned with beautiful red-brick buildings starkly contrasting the sparkling blue of the sea is beloved by the Instagrammers. One must come to the seafront for a late dinner when the sunset lights the sky with fire and casts a magnificent warm glow onto the house reflections in the water. The in-town features old-fashioned board houses intermixed with impressive colonial buildings and spaced by fresh green spaces calling to set a picnic and relax within the immense scenery. 

These truly-magical towns come with scenery that makes one rub their eyes to believe that it is real. From stunning waterfronts to magnificent state parks, rolling hills, and other scenic spectacles, one will be immersed in the freshest environment full of sights to attain the truly deserved relaxation for the body and the mind.

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