8 Of The Most Captivating Small Towns In Connecticut

This year or the next, connect to some of the most captivating small towns in Connecticut. In a state so named after the Connecticut River—which in turn got its name from the Mohegan word “Quonehtacut,” meaning "long tidal river”—travelers will be enlightened by new insights into America’s past in historic towns such as Kent and Cornwall. Additionally, you will get to know all about the indigenous cultures in Connecticut in welcoming communities like Branford and Washington, while towns like Mystic and Old Saybrook give visitors a grand appreciation of the Constitution State’s many waterways. Last of all, you will be awestruck by the many captivating small towns in the most pivotal state of the original 13 colonies that openly defied the British Empire.

Cornwall

Cornwall, approximately 42 miles from the city of Hartford in the Berkshire Mountains, is a town of many titles. It has been lauded by travelers and locals alike for being the “greenest town” in Connecticut, the “Home of the Covered Bridge” because the historic West Cornwall Covered Bridge was built in 1864, and a place where “The mind, eager for caresses, lies down at its own risk in Cornwall” by the poet Mark Van Doren. This small town that got its name from the county of Cornwall in England certainly lives up to its many titles and praises, and you can create new titles for Cornwall yourself when exploring the Wyantenock State Forest, Mohawk State Park, and Housatonic Meadows State Park. One can also admire the former homesteads of the founders of Vermont, Ethan Allen, and Ira Allen, as well as the home of another author named James Thurber and the house of a Broadway producer named Oscar Serlin. No need to feel unwanted in Cornwall, especially when you are staying in the welcoming hearths at the Cornwall Inn.

Kent

One cannot get enough of the small town of Kent. Only about 18 minutes from Cornwall, an author named Eric Sloane, who wrote over 38 books, used to live in Kent, which the Eric Sloane Museum explores. Meanwhile, the Kent Iron Furnace is one of a few historic ruins that helped develop Kent into the industrial age. For those of you eager to go venturing into the outdoors, you can always journey to the Macedonia Brook State Park for scenic sights of the Taconic Mountains and the Catskill Mountains, or perhaps take the Appalachian Trail all the way to the Kent Falls State Park and Falls Brook. Naturally, you can also admire Kent Falls, which gave the town its name, although it was originally called “Scatacook” by the Native Americans who once inhabited the area. So, if you are enthusiastic about seeing more of Kent’s attractions, you ought to at least book a room at either the Cooper Creek Bed & Breakfast or The Spirit Horse Farm.

Essex

The resplendent town of Essex on the Connecticut River is an excellent destination in the Lower Connecticut River Valley Planning Region. Only about 32 miles west of New Haven, travelers will be amazed by the different attractions within the three communal towns that compose Essex—these being Centerbrook, Ivoryton, and Essex Village. A complex called the Ivoryton Playhouse at Ivoryton offers several venues for local performances. Meanwhile, one can board a schooner cruise that goes through the Connecticut River in the district of Essex Village. Lastly, you can ride a vintage train known as the Essex Steam Train at Centerbrook, which is connected to other nearby towns and cities in the Lower Connecticut River Valley Planning Region. If you are excited about more sights, then head over to The Preserve for some birdwatching detours, or you can always spend your evenings in humble accommodations such as the Griswold Inn, Safe Harbor Essex Island, or Copper Beech Inn.

Old Saybrook

Old Saybrook, about nine minutes away from Essex, is a good place to learn all about some of Connecticut’s historic past. On land that formerly belonged to the Algonquin-speaking peoples of the Nehantic and Pequot, Old Saybrook was initially visited by Dutch traders who established a brief presence before the English Puritans permanently settled the area in 1635 as part of the Saybrook Colony. Many of the historic New England buildings along the Connecticut River have retained their original designs, as best seen in either the General William Hart House—with its artifacts of a famous leader during the American Revolutionary War—or Fort Saybrook Monument Park. Regions like the Ferry Landing State Park and Harvey’s Beach promise leisurely boat tours of the Connecticut River and Long Island Sound, where herons and ospreys are in abundance. Fine lodgings like the Saybrook Point Resort & Marina and the Pier Blue Inn will allow you to sleep peacefully after a long day of vacationing in Old Saybrook.

Branford

In the year 1638, after 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 a land once known as Totokett, commonly believed to mean 'Tidal River,' the town of Branford soon rose up to be one of the oldest communities in Connecticut. Only six miles away from New Haven, Branford has retained much of its old New England splendor minus the British Empire’s colonialist administration, and newcomers will be astounded by the excellent craft beers of the Thimble Island Brewery, Duvig Beer Company, and Stony Creek Brewery. In homesteads like the Harrison House Museum, one can see what the Americana lifestyle was like, while magnificent destinations like the Lake Saltonstall Recreational Area will keep you entertained and rejuvenated for the outdoors. Should you desire a more extended stay in Branford, you can always seek accommodations at either the Owenego Inn or American Inn.

Mystic

On the Mystic River lies the town of Mystic, which is similarly named. Since the 19^th century, shipwrights, blacksmiths, builders, and seafarers have called Mystic their home away from home and have contributed much to the town’s development. One can learn all about Mystic’s historic chapters at the Mystic Seaport Museum. You can also admire Charles W. Morgan, the last wooden whaleship preserved in the US. The Mystic River Bascule Bridge leads travelers toward the Mystic Aquarium, where one can admire the marine wildlife in the Mystic River. Meanwhile, the Mystic Museum of Art exhibits numerous masterpieces from Mystic’s artisans. Mason’s Island’s Tree Trails will leave you mesmerized by all the mystical flora and foliage surrounding the town, and majestic abodes like the Inn at Mystic, The Whaler’s Inn, and Harbor View Landing will have you wanting to see more of Mystic’s wonders.

Westport

Lounging beside the Saugatuck River, Westport promises visitors a once-in-a-lifetime vacation. Only about 52 miles from New York City, many of you might be familiar with the town even if you never actually stepped foot on it. That is because Westport has been the setting of several American TV series, among them Billions, American Housewife, The Sisterhood of the Traveling Pants 2, The Stepford Wives, and more. For a more vicarious experience of Westport, you can watch lively performances at Levitt Pavilion or traipse through Cockenoe Island in Long Island Sound, in addition to Sherwood Island State Park’s beaches and shorelines. Compo Beach, meanwhile, contains the remains of British cannons left behind after their defeat in the Revolutionary War. So, in this town founded by five Bankside Farmers in Westport in 1648, give yourself a much-desired getaway from the big cities in accommodating hostels like The Inn at Longshore.

Washington

Approximately 50 miles from the city of Hartford, the small town of Washington welcomes visitors to a handful of attractions along the Shepaug River. Whether you are kayaking through Lake Waramaug or gallivanting across the green pastures if Litchfield Hills, you will undoubtedly be amazed by the natural sceneries surrounding this small town so named after President George Washington. At the Institute for American Indian Studies (IAIS), one can learn all about the Native American tribes that once thrived in Connecticut. Elsewhere, the Judea Parish House, the Smithy Loft Gallery, and St. John’s Church are among the many historic structures that showcase an inkling of early Americana life—many of these buildings were made by a single architect, whose name was Ehrick Rossiter. However, more modern buildings like the Mayflower Inn & Spa, Windemere Bed & Breakfast, and Hopkins Inn are more suitable for nightly and daily accommodations than tourist appeal. So, whatever you intend to do in Washington, do so with aplomb and appreciation.

Discover Connecticut’s Timeless Charm

In the land where the first Thanksgiving was held in 1621 and where the oldest US-based newspaper, The Hartford Courant, continues to stay relevant, Connecticut contains a number of captivating small towns for you to visit this 2024 and beyond. From Westport’s recognizable locales to Old Saybrook’s architecture reminiscent of Europe’s old towns, travelers will find many things, both old and new, to cherish upon one’s homely return. So go exploring in the homeland of ESPN and Yale University, and use that freedom that Connecticut fought the British Empire to give you in fruitful and fantastic explorations in the most captivating small towns in Connecticut.