8 Undiscovered Small Towns in Connecticut
From the Mohegan word Quonehtacut, meaning "long tidal river," as a reference to the Connecticut River, the state of Connecticut is strangely the fourth most densely populated urban/suburban area and the third smallest state in the United States. With this small, tightly-packed state are a number of undiscovered small towns in Connecticut for you to cherish and explore. There are, for instance, humble and bucolic towns like Kent and Cornwall that are replete with nature’s wonders and historic appeal. Then there are mystical, seaside towns like Mystic and Old Saybrook that have contributed much to Connecticut’s industry via the Connecticut River. And there are also towns like Branford and Washington that continue to showcase the Indigenous cultures of Connecticut. In 2024, discover more from these overlooked and hidden towns in the beautiful state of Connecticut.
Essex
Essex is a trinity of beautiful attractions and wonders in the Lower Connecticut River Valley Planning Region. Only about 32 miles from the city of New Haven and lounging on the Connecticut River, Essex is an amalgam of three distinct villages called Centerbrook, Ivoryton, and Essex Village. At the Ivoryton Playhouse, you can be sure to feel entertained by the magnificent performances in the playhouse. At Centerbrook, hop aboard the Essex Steam Train for old-school rides through the tri-towns or in other nearby villages in Connecticut.
Finally, at Essex Village, you can take a schooner cruise down the waters of the Connecticut River. Essex is also a grand destination for birdwatchers, especially in the wildlife sanctuary called The Preserve. Once all the explorations get you exhausted, rejuvenate in fine lodgings like the Copper Beech Inn, the Griswold Inn, or Safe Harbor Essex Island.
Cornwall
About 42 miles from Hartford, visitors will be entreated to the “greenest town” in Connecticut, Cornwall. So named after the county of Cornwall in England, the town of Cornwall is a convenient entranceway to the Berkshire Mountains. As the “Home of the Covered Bridge,” you can traverse the historic West Cornwall Covered Bridge, which has been in use since 1864. The poet Mark Van Doren once described Cornwall as a place where “The mind, eager for caresses, lies down at its own risk in Cornwall.” One can lie down specifically in heavenly parks like the Housatonic Meadows State Park, Mohawk State Park, and the Wyantenock State Forest.
In addition to being a beautifully bucolic backyard in Connecticut, Cornwall happens to be the former home of Ethan Allen and Ira Allen, the founders of Vermont; Oscar Serlin, a Broadway producer; and an author named James Thurber. So should you ever wish to explore more of Cornwall, do consider booking a room at the Cornwall Inn.
Kent
Approximately 18 minutes from Cornwall, Kent is home to the Eric Sloane Museum, which was once the gallery of the author and illustrator Eric Sloane, who has written over 38 books, as seen in his museum. There are also the ruins of the Kent Iron Furnace, which has contributed much to Kent’s industrial development, and the Kent Falls State Park, which is connected to the renowned Appalachian Trail and the mountain stream of Falls Brook.
Nature lovers will enjoy leisurely strolls through the Macedonia Brook State Park, where one can take panoramic pictures of the Catskill Mountains and the Taconic Mountains. You will also fall in love with Kent Falls, a 250-foot waterfall that was originally called “Scatacook” by the Native Americans. No need to worry about accommodations, because the Cooper Creek Bed & Breakfast and The Spirit Horse Farm have you covered for your stay in Kent.
Old Saybrook
Approximately nine minutes from Essex, Old Saybrook was formerly an Algonquin dwelling place of the Nehantic and Pequot Native Americans before immigrants from Europe—particularly from the Netherlands—established a town along Connecticut’s Gold Coast. Old Saybrook sits where the Connecticut River flows out into the Long Island Sound, and many of the Dutch and New England homesteads in the town have remained unchanged over the centuries. The Ferry Landing State Park promotes scenic ferry cruises through the Connecticut River and Long Island Sound, while Harvey’s Beach brims with flocks of ospreys and herons.
At the General William Hart House, you can peruse the articles and memorabilia of a renowned leader from the American Revolution. The Fort Saybrook Monument Park further highlights Old Saybrook’s contributions and events during the Revolutionary War. For those of you intrigued by Old Saybrook’s archaic charms, you can pick either the Saybrook Point Resort & Marina or the Pier Blue Inn as suitable establishments to spend your evenings.
Branford
Branford is a quaint and soothing vacation spot for those wanting to experience the waters of the Long Island Sound and the Thimble Islands. One of the oldest towns in Connecticut since 1638, Branford was established by New Haven colonists when they traded "eleven coats of trucking cloth and one coat of English cloth made in the English fashion" to the Mattabesec tribe in a land originally called Totokett or “Tidal River.”
One can peruse the exhibits of the Harrison House Museum to acquaint yourself more about Branford’s past, or you can tour the popular breweries of Stony Creek Brewery and Thimble Island Brewery. Since Branford is renowned for its watery wonders, you might want to pack a picnic or swimwear to the Lake Saltonstall Recreational Area or to one of the many beaches on the coastline. Only six miles east of New Haven, you will feel right at home in awesome lodgings like the Owenego Inn or American Inn.
Mystic
Be enchanted by the mystic charms of Mystic, a seaport town on the eponymous Mystic River. In the 19th century, Mystic was a nexus of development and commerce for shipwrights, blacksmiths, builders, and seafarers. The Mystic Seaport Museum tells the many tales of Mystic’s men and women who gave much to the community, just as Charles W. Morgan serves as the last wooden whaleship still in service in the US. Those with more modern and avant-garde tastes can visit the Mystic Museum of Art for its exquisite exhibits, or you can traverse the Mystic River Bascule Bridge towards the Mystic Aquarium for its aquatic wildlife.
For further relaxation and adventures, visit Mason’s Island or trek through the TreeTrails. And for those of you who need accommodations, look to the Inn at Mystic, The Whaler’s Inn, or Harbor View Landing for your daily and nightly needs.
Westport
About 52 miles from New York City and on the banks of the Saugatuck River, you will find the delightful abodes of Westport. Ever since the five Bankside Farmers founded Westport in 1648, the town has grown into a rejuvenating retreat for many of New York City’s citizens. Many of you might recognize the town’s settings from notable American TV and movies such as Billions, American Housewife, The Sisterhood of the Traveling Pants 2, and The Stepford Wives. Many of these silver and blue screen references include Cockenoe Island, which is located in Long Island Sound, as well as the sublime beaches and picnic spots at the Sherwood Island State Park.
There is also a speck of history in Westport, as seen in Compo Beach, where the remnants of British cannons from the Revolutionary War in 1777 lie idle and unarmed. While in Westport, you should definitely watch performances at Levitt Pavilion in its downtown. If you are interested in vacationing in Westport, book a room in one of the many establishments in town, like The Inn at Longshore.
Washington
The town of Washington in Connecticut may not be as famous as Washington DC, but it certainly has a number of New England amenities for you to cherish. Go wading through the waters of Lake Waramaug and the Shepaug River, or sojourn through the rolling green of the Litchfield Hills. If the splendors of nature are not sufficient, then you can always tour the Institute for American Indian Studies (IAIS), a modern museum chronicling and highlighting the various Indigenous cultures that have called Connecticut their home.
Afterward, explore the vestibules and halls of the Judea Parish House and St. John’s Church—among the many historic buildings in Washington, some of which were designed by American architect Ehrick Rossiter. Only 50 miles from Hartford, savor the laidback accommodations of the Mayflower Inn & Spa, or nearby Windemere Bed & Breakfast, and Hopkins Inn.
The Constitution State of Connecticut—the most influential of the 13 original colonies that defied the British Empire—has many small towns undiscovered by many tourists who are looking for a break from the big cities or are seeking simple and pleasurable places to explore. Connecticut will have you connecting to the modern community, the Indigenous cultures, and the compelling past of the US. So in a state where Yale University, and The Hartford Courant—the oldest US-based newspaper still being published—continues to operate, be sure to uncover the many wonders and secrets of the many undiscovered small towns in Connecticut.
