View from Westport bridge over Saugatuck river and architecture near downtown in beautiful spring day

8 Cutest Small Towns in Connecticut

Also known as the “Constitution State”, beautiful Connecticut was admitted to the Union in 1788 and continues to be a place of fascinating historic intrigue and unique coastal beauty. Indeed with some 310 miles of shoreline, much of Connecticut has charming and stunning towns with wonderful vistas. Add in important American history, welcoming hospitality, and loads of scenic panoramas, and a trip to Connecticut’s towns will surely be a most memorable time for the whole family.

Westport

Westport downtown waterfront view
Westport downtown waterfront view

Just 52 miles from New York City, the beautiful town of Westport was first established in 1835 and is now home to a population of just over 27,000 residents. With not one, but three great beach areas, Westport is indeed a great place to discover for families and the solo tourist alike. Stop by the Old Mill Beach, where a quiet and relaxing afternoon is always sought after or take in the sun and stunning waterfront views at Compo Beach.

Aerial view shot of Westport
Aerial view shot of Westport, showing the Saugatuck River

Meanwhile at the Sherwood Island State Park, an area spanning some 230 acres offers its guests some of the State’s best panoramas. And of course even just a casual stroll though the town’s Historic District or along the Saugatuck River is a great way to spend a few hours.

Mystic

Mystic Seaport, is an outdoor recreated 19th century village and educational maritime museum. Visitors will find a lighthouse replica of Brant Point Light.
Mystic Seaport, is an outdoor recreated 19th century village and educational maritime museum. Visitors will find a lighthouse replica of Brant Point Light.

The town of Mystic is a most beautiful seaside escape, with a most modest population just over 4,000 residents. Within a close driving distance of many beach areas, Mystic itself is home to the wonderful Williams Beach Park, Esker Point Beach, and DuBois Beach where calming sea vistas always delight. In addition the town’s three historic districts continue to make Mystic one of Connecticut’s most perennially popular tourist stops. Explore the Mystic Seaport Museum, the Museum of Art, or the Mystic Aquarium, when in this New England town there is never a shortage of historical, cultural, and natural splendor to be fully appreciated.

Madison

Blue hour after sunset in Madison Connecticut from East Wharf beach
Blue hour after sunset in Madison Connecticut from East Wharf beach

Formally incorporated in 1826 and named after the fourth American President James Madison, the town of Madison is indeed a splendid slice of Connecticut’s beautiful coastline. Home to a population of just under 18,000 inhabitants, visitors to the town will find great natural surroundings and fascinating historic intrigue. Enjoy a healthy dose of quaint and charming galleries, shops, local restaurants, and 19th century buildings, many of which form part of the National Register of Historic Places. And for the outdoors seeker, spending time at Hammonasset Beach State Park is always a popular activity. Attracting up to one million visitors annually, one can partake in such fun ventures like fishing, swimming, sailing, biking, and picnicking in a most picturesque locale.

Greenwich

 sailboat is moored in front of a luxury waterfront estate in Greenwich, Connecticut
 A sailboat is moored in front of a luxury waterfront estate in Greenwich, Connecticut

Situated on Connecticut’s Gold Coast and often stereotypically associated with the “Connecticut Blue Blood”, Greenwich is a pleasant and beautiful town for visitors of all ages. First settled back in 1640, this historic town houses many historic neighborhoods and landmarks, in addition to great museums and a bustling restaurant scene. Visit Great Captain Island and its lighthouse (1829) for some majestic seaside vistas, and now part of the National Register of Historic Places. Meanwhile at Greenwich Point beach, opportunities for swimming, sailing, fishing, jogging, and cycling keep visitors occupied in a most beautiful ambience. And with its comfortable year round temperatures, exploring Greenwich no matter what the season is always a good idea.

Old Saybrook

Summer sunset in Old Saybrook along the Connecticut River with Lynde Lighthouse in the foreground and a summer sunset By Gregory on Adobe Stock
Summer sunset in Old Saybrook along the Connecticut River with Lynde Lighthouse in the foreground and a summer sunset By Gregory on Adobe Stock

Old Saybrook is one of Connecticut’s most scenic towns and is stunningly settled right at the mouth of the Connecticut River. Founded in 1738, the modern town of 10,481 residents welcomes visitors with its delightful attractions including the Fenwick Historic District, the Saybrook Breakwater Lighthouse (constructed in 1886), and a number of landmarks on the National Registry of Historic Places. Meanwhile for beach lovers a stop at Harvey’s Beach is a cannot miss. Here soothing sands and calming waters make this a true Connecticut paradise. Go swimming, leisurely walk along the shoreline, listen to local artists performing their music, or try some of the local treats from stationed vendors, when in Old Saybrook the charm is never in short supply.

East Lyme

Tranquil view Niantic Connecticut salt marsh in summer with blue sky and blue boat reflections of cumulus clouds in still water with copy space, saltwater tidal marsh, East Lyme
Tranquil view Niantic Connecticut salt marsh in summer with blue sky and blue boat reflections of cumulus clouds in still water with copy space, saltwater tidal marsh, East Lyme

With its beautiful shoreline vistas and a most charming one and half mile boardwalk, the town of East Lyme is a place where panoramas are never in short supply. Spend time at Hole in the Wall Beach or the McCook Park Beach, where soft white sand, sparkling waters and pleasantly warm sun attract visitors year round. Meanwhile at the Rocky Neck State Park Beach, rocky shores, and a tidal river contrast with the more relaxing image of traditional beaches for a most unique experience. And with plenty of welcoming hospitality, great local restaurants, and several historic sites to be discovered, East Lyme truly is a most special Connecticut community.

Colebrook

Colebrook, Connecticut USA A country road along the cornfields
Colebrook, Connecticut USA A country road along the cornfields

Colebrook is a sleepy town that traces its colonial history back to 1779, just after the beginning of the American Revolution. Home to a population of just over 1,300 residents, Colebrook is filled with a genuine small town charm nestled beautifully within rolling hills and lush greenery. In the fall the splendid colours of red and yellow make for an even more stupendous visual delight, while time spent at the Gaylord Pond Dam is always a relaxing outing. Meanwhile at the nearby Haystack Mountain Observation Tower some of the best panoramas of the region can be observed, ideal for an afternoon excursion for the whole family.

Guilford

Streetview in Guilford square
Street view in Guilford square

First settled back in 1639, Guilford is indeed one of the United States’ oldest towns and continues to preserve its centuries worth of history. Indeed visitors to this town of 22,000 residents will see loads of homes, buildings and other landmarks from the 17th, 18th, and 19th centuries. Explore a number of sites on the National Register of Historic Places (including the Acadian House from 1670), tour fascinating local museums, and of course browse through the charming selection of restaurants and boutique shops in the downtown area. In addition for the outdoors lover, Guilford also offers pretty beach areas which include the popular Jacobs Beach. Here activities likes sailing, swimming, hiking, and biking can all be enjoyed in a 25 acre area.

The State of Connecticut is a stunning component of America’s New England region, filled with sublime coastal beauty and intriguing historical charm. With its mix of unique shorelines, fascinating town histories, and loads of warm hospitality, the “Constitution State” and its towns are great places to spend a holiday in. Whether it is for a weekend excursion or a longer stay, or travelling solo or with family, when in these wonderful Connecticut towns, special memories will surely always follow.

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