The Mystic bascule bridge spans the Mystic river, in Mystic, Connecticut. Image credit Paul Latham via Shutterstock

9 Most Memorable Small Towns in Connecticut

Even though Connecticut is the third smallest state in the US, it is the fourth most populated urban/suburban area in the country. So named after the Connecticut River (from the Mohegan word "Quonehtacut" meaning "long tidal river"), travelers from all over will never forget their experience in Connecticut, especially in the most memorable small towns of the state. From picture-perfect villages like Kent, Essex, and Cornwall to popular seaside towns like Old Saybrook and Mystic along Connecticut's Gold Coast, these small towns will never fall into oblivion. So head on to these towns like Yankee Doodle (the state anthem), and whether you are riding on a pony or calling a feather a macaroni, you will definitely be feeling the New England charm of Connecticut.

Kent

Connecticut Antique Machinery Association in Kent, Connecticut. Image credit Marcelo Murillo via Shutterstock
Connecticut Antique Machinery Association in Kent, Connecticut. Image credit Marcelo Murillo via Shutterstock

The humble town of Kent is a sublime mix of old-school and avante-garde. Only about 18 minutes from Cornwall, visitors can follow the rolling mountain stream of Falls Brook towards either the grand Appalachian Trail or the soothing Kent Falls State Park. The cascading 250-foot Kent Falls, once called "Scatacook" by the Native Americans who fished in the area, creates the widespread Housatonic River that feeds much of the forestry in Kent. One might also be interested in hiking and camping in the Macedonia Brook State Park for views of the Catskill and Taconic mountains.

Afterwards, you can tour the Eric Sloane Museum, the gallery of famed artist, author, and illustrator of over 38 books, Eric Sloane. In the museum, early Americana artifacts speak about how life was lived in the 19th century. Consider visiting the Kent Iron Furnace ruins to learn more about Kent's iron industry. For places to stay, the Cooper Creek Bed & Breakfast and The Spirit Horse Farm are a few good establishments to spend the night.

Essex

Antique train at Essex Train Station in Essex Connecticut
Antique train at Essex Train Station in Essex, Connecticut.

About 32 miles from New Haven is the lovely town of Essex. As part of the Lower Connecticut River Valley Planning Region, Essex comprises three villages: Essex Village, Centerbrook, and Ivoryton. This triumvirate shares the Connecticut River and the conjoined attractions in the area. Visitors can delight in award-winning performances at the Ivoryton Playhouse or board the Essex Steam Train in Centerbrook.

In Essex Village, one can enjoy schooner cruises down the famous Connecticut River. You might also fancy trekking through The Preserve, a wildlife sanctuary for numerous avian species. No need to worry about lodgings because the Copper Beech Inn, the Griswold Inn, and Safe Harbor Essex Island will provide excellent accommodations for you.

Cornwall

Beautiful St. Bridget's Church near Housatonic River in Cornwall, Connecticut.
St. Bridget's Church near Housatonic River in Cornwall, Connecticut. Image credit Miro Vrlik Photography via Shutterstock.com

Cornwall, so named after the county of Cornwall in England, is widely regarded as Connecticut's "greenest town" due to its location in the foothills of the Berkshire Mountains. With a 42-mile proximity from Hartford, this majestic town is the kind of place where "The mind, eager for caresses, lies down at its own risk in Cornwall," as local poet Mark Van Doren once wrote. You can delight in the liberating atmosphere of the Housatonic Meadows State Park, Mohawk State Park, or the Wyantenock State Forest.

As a haven for artists, visit the innumerable galleries and studios that showcase the astonishing pieces Cornwall promotes. You should also visit the homes of many renowned individuals like Ethan Allen and Ira Allen, the founders of Vermont, the author James Thurber, and Broadway producer Oscar Serlin. Cornwall is also called the "Home of the Covered Bridge" as homage to the West Cornwall Covered Bridge that has been used since 1864. After a day on the town, consider staying at the Cornwall Inn.

Old Saybrook

Gorgeous Lynde Point Lighthouse, Old Saybrook, Connecticut.
Gorgeous Lynde Point Lighthouse, Old Saybrook, Connecticut.

Old Saybrook is a nine-minute-away neighbor of Essex and rests along Connecticut's Gold Coast. Once home to the Algonquin Nehantic and Pequot Native Americans before European settlers arrived, the town is precisely where the meandering Connecticut River spills out into the Long Island Sound. Much of the New England and Dutch architecture is predominantly showcased throughout the town.

Visitors can charter ferry trips out of the Connecticut River and all over the Sound at the Ferry Landing State Park or under the Baldwin Bridge on Ferry Road. Head to Harvey's Beach to watch flocks of herons and, ospreys and other magnificent birds ride the sea winds. Or you can tour the General William Hart House, former residence of a renowned Revolutionary leader, and the Fort Saybrook Monument Park to learn more about the port town's value as a military location. Lastly, you can settle down at the Saybrook Point Resort & Marina or the Pier Blue Inn.

Branford

Dusk at the Pier, captured during the winter in Stony Creek, Brandford Connecticut
Dusk at the Pier, captured during the winter in Stony Creek, Brandford, Connecticut.

The quiet town of Branford is located 6 miles east of New Haven. Its proximity to the Long Island Sound and the Thimble Islands makes Branford a perfect getaway from the bigger cities of Connecticut. Branford is also one of the oldest towns in the state since 1638 when the New Haven Colony traded "eleven coats of trucking cloth and one coat of English cloth made in the English fashion" to the Mattabesec tribe for land known as Totokett or "Tidal River." The Harrison House Museum commemorates that occasion and many more.

These days, Branford is renowned for three popular breweries: Stony Creek Brewery, Thimble Island Brewery, and Duvig Beer Company. Consider purchasing a beer in one or all of these fine places while strolling through the Lake Saltonstall Recreational Area or along the many beaches overlooking the sound. Most importantly, book a room at the Owenego Inn or American Inn.

Mystic

The seaport in Mystic, Connecticut.
The seaport in Mystic, Connecticut. Image credit Faina Gurevich via Shutterstock.com

The mystical village of Mystic is an excellent seaport town to explore. Memorabilia and artifacts of the town's 19th-century shipwrights, builders, blacksmiths, and seafarers can all be appraised in the Mystic Seaport Museum. The main attraction there that history buffs and seafaring enthusiasts will love is the commercial vessel, the Charles W. Morgan, the last wooden whaleship still afloat in the US. In addition, the Mystic Museum of Art promotes the artistic and cultural society along the Mystic River. For rare and unique treats, venture across the historic Mystic River Bascule Bridge and marvel at the wonderful marine animals in the Mystic Aquarium. Head to Mason's Island for a bevy of retreats and relaxation. Finally, unleash the inner daredevil in you by braving the Tree Trails. If you ever get tired, relax at the Mystic Inn, The Whaler's Inn, and Harbor View Landing.

Chester

People gather for a Winter Festival in Chester, Connecticut.
People gather for a Winter Festival in Chester, Connecticut. Image credit Joe Tabacca via Shutterstock.com

Just 10 minutes north of Essex is the rural town of Chester. Like Essex and Old Saybrook, Chester is part of the Lower Connecticut River Valley Planning Region and, as such, offers a prime cruise through the Connecticut River from the Chester/Hadlyme Ferry. Similarly, the medieval Gillette Castle presents a spectacular view of the Connecticut River. If you stroll around Pattaconk and Cedar Lakes, and Camp Hazen, you might spot Chester's community animals, the squirrels. Aside from squirrels, Chester is also home to a handful of Chakana sky alpacas in a nearby alpaca farm. But the town is prominently known for theatrical performances at the world-renowned Goodspeed Opera House.

Westport

View from road one to Church Lane in beautiful spring day with Patagonia store and Anthropologie store, Westport, Connecticut.
Downtown, Westport, Connecticut. Image credit Miro Vrlik Photography via Shutterstock

The sunny town of Westport lounges on the banks of the Saugatuck River. Located about 52 miles from New York City, Westport serves as a splendid retreat from metropolitan chaos. Much of the seaport town's history is centered on its television-worthy landscape. Popular shows and movies like Billions, American Housewife, The Sisterhood of the Traveling Pants 2, and The Stepford Wives were inspired or filmed in Westport's New England setting.

Visitors ought to head to Cockenoe Island for a closer experience of Long Island Sound. Afterward, stroll through the beaches and picnic areas of Sherwood Island State Park. On Compo Beach, you will find British cannons left behind during the Revolutionary War in 1777. Levitt Pavilion in downtown Westport promotes sublime performances of art and music. And stay awhile in this town founded by the five Bankside Farmers of 1648 by finding excellent accommodations at The Inn at Longshore.

Washington

Bryan Memorial Town Hall in Washington, Connecticut.
Bryan Memorial Town Hall in Washington, Connecticut. Image credit Ritu Manoj Jethani via Shutterstock

Want to experience a different kind of Washington other than Washington, DC? Then, head on to the small town of Washington in Connecticut, only about 50 miles away from Hartford. The town is embraced by several natural attractions, such as Lake Waramaug, the Shepaug River, and the Litchfield Hills. Parallel to these ecological gems are Washington's cultural and historic amenities. For example, the Institute for American Indian Studies (IAIS) serves as a museum dedicated to the preservation and education of the Native American peoples in the Connecticut region.

Among the numerous New England architecture that one can gawk at are the Judea Parish House, the Smithy Loft Gallery, and St. John's Church. Most of these buildings were designed by renowned American architect Ehrick Rossiter. When it comes to rest and relaxation, fine lodgings like Mayflower Inn & Spa, Windemere Bed & Breakfast, and Hopkins Inn.

Connecticut is best called the Constitution State since it was among the most influential of the original 13 colonies. To this day, Connecticut remains influential because it is the home base for industries like ESPN, Yale University, and The Hartford Courant, the oldest US-based newspaper still being published. But it is the small towns of the Constitution State that will affect how you enjoy the simplicity and quaintness of life. Get ready to fall in love in a state where the first Thanksgiving was held in 1621. Whether humble villages like Washington and Westport leave you wanting for more, or unique settlements like Chester and Branford entice you to stay, these Connecticut small towns will always be remembered.

Share
  1. Home
  2. Places
  3. Cities
  4. 9 Most Memorable Small Towns in Connecticut

More in Places