8 Most Inviting Towns in Connecticut

Connecticut is a historically fascinating and geographically beautiful Northeastern State that forms a key component of America’s famed New England Region. Admitted to the Union in 1788, the “Constitution State” is home to some 300 miles of stunning shoreline, and its welcoming towns are indeed true wonders for any traveler looking to discover unique Americana. Indeed, whether it is a weekend getaway or a longer sojourn, Connecticut’s inviting towns are filled with natural splendor, American history, and loads of New England charm. So take to the road and come what makes Connecticut a cannot miss destination for anyone in the Northeastern United States.

Westport

The historic town of Westport is beautifully located on Connecticut’s Gold Coast and is conveniently located just some 48 miles from New York City. Established in the 1830s, today, this inviting community of just over 27,000 residents remains one of the State’s most beautiful beach destinations. A perfect place for a summer weekend getaway, tourists can enjoy a number of splendid beach areas in Westport, which include Compo and Old Mill Beaches. Here, golden sands and superb coastal views of the Atlantic Ocean make it a most picturesque and relaxing spot for the entire family. And, of course, one cannot forget about the grand Sherwood Island State Park, which spans an impressive area of some 230 acres! Finally, history lovers can also appreciate Westport, and an afternoon exploring the historic district is a great way to learn more about Connecticut’s past. Marvel at a number of preserved 19th-century edifices and landmarks while the quiet sounds of the nearby Saugatuck River create a most charming and quaint ambiance.

Colebrook

Colebrook was founded during the American Revolutionary War in the 1770s, and today it boasts a modest population of just over 1,300. A charming and sleepy community that is steeped in history, Colebrook’s natural beauty also makes it an attractive place to discover firsthand. Surrounded by rolling hills and splendid, lush greenery, Colebrook is indeed a most peaceful small Connecticut town ideal for a few days’ getaway. Indeed, whether it is summer, autumn, or winter, Colebrook has something picturesque to offer. From multi-colored foliage in the Fall to shining silver snow tops in the winter, there is never a shortage of beautiful sights to enjoy here. Encounters with raw nature are a delight at the nearby Gaylord Pond Dam. Add in a cute assortment of local restaurants, cafes, shops, and other businesses, and historic landmarks like the Rock Hall Mansion (1911), and Colebrook truly stands out as a postcard-perfect outing for all those in the “Constitution State.”

Madison

Another beautiful Connecticut beach town, Madison, was established in the 1820s and named after President James Madison. Featuring a wonderful mix of historic allure and a splendid natural ambiance, Madison is indeed one Connecticut town that all ages can enjoy. With a population of nearly 18,000 residents, guests can explore a number of preserved 19th-century landmarks, including the Madison Green Historic District and Allis Bushell House (1785), amongst others listed on the National Register of Historic Places. Add in a welcoming array of local restaurants, shops, and galleries, and the small-town charm of Madison is never in short supply. Meanwhile, for the outdoors lover, this town is also a great destination that you cannot miss. Take in the sun at the very popular Hammonasset Beach State Park, where millions of tourists descend each year. Enjoy such activities as sunbathing, swimming, sailing, fishing, picnicking, and cycling in a most beautiful and picturesque hot spot.

East Lyme

Founded in the 1830s, the town of East Lyme is home to a modern population of just under 19,000 inhabitants. A scenic community known for its picturesque shoreline and its inviting boardwalk, spending time in East Lyme will surely not disappoint. Enjoy some beautiful outdoor areas that are popular with travelers of all ages, including the Rocky Neck State Park Beach, Hole in the Wall Beach, and McCook Park Beach, amongst others, where warm sun, rocky shores, and welcoming small-town ambiance abound. Meanwhile, the charming villages of Niantic and Flanders (located entirely within the town) are great ways to spend an afternoon enjoying some of the best of small-town New England. Explore some restored 19th-century buildings, marvel at pretty beach houses, and take in the incredible assortment of local shops, restaurants, and other businesses. Indeed, East Lyme is one of Connecticut’s most inviting and unique places.

Old Saybrook

Old Saybrook is beautifully located on the mouth of the Connecticut River, making it one of the State’s most beautifully picturesque locales. Established in the 1730s and how home to a population of just under 10,500 inhabitants, Old Saybrook is indeed a most inviting seaside town where great natural beauty and unique cultural and historical allure come together. Explore the sights and sounds of the Fenwick Historic District and marvel at landmarks like the Breakwater Lighthouse (1886), amongst others included on the National Register of Historic Places. From there, browse the charming array of restaurants, shops, and other galleries on the pleasant Main Street, where some of the best of small-town New England can be found. And, of course, with Old Saybrook’s vicinity to the water, any trip here would be incomplete without enjoying opportunities to go swimming and sailing. Spend an afternoon at Harvey’s Beach, where, in addition to lounging, live entertainers and tasty food vendors dot the landscape, making it an ideal stop for the entire family.

Chaplin

A modest community of just over 2,000 inhabitants, Chaplin can trace its modern history to the early 1820s. A scenic and historically alluring place of discovery, the town remains a most inviting destination to enjoy the beauty of nature and genuine Americana. Explore the Chaplin Historic District and its collection of preserved 19th-century landmarks, including the Witter House (1820), which is listed on the National Register of Historic Places. Add in splendid panoramas filled with colorful foliage, pristine green lawns, and stately brick house architecture, and Chaplin is indeed a picture-perfect outing for any traveler. In addition, Chaplin also boasts a charming array of welcoming bed and breakfast establishments like the Henrietta House in nearby Ashford. Enjoy a relaxing sojourn in an old fashioned setting and see what makes this a most special town typical of the beloved New England.

Mystic

A charming seaside destination, the town of Mystic can trace its history to the 1780s when it served as one of Connecticut’s most important ports. Home to a modern population of just over 4,000 residents, Mystic maintains an inviting historic allure coupled with a beautiful natural ambiance. Explore such attractions as the Seaport Museum, the Museum of Art, and the Mystic Aquarium, ideal for both solo travelers and families alike. Meanwhile, a fine assortment of local shops, restaurants, and other galleries give the town a genuine feeling of typical New England life. And, of course, one cannot miss out on Mystic’s beautiful beach areas, which include Williams Beach Park, Esker Point Beach, and DuBois Beach. Here, the warm sun and shining blue Atlantic waters make it a nice place to enjoy a relaxing summer outing, all within the confines of a quintessential New England town.

Guilford

Established way back in the 1640s, Guilford is one of the oldest colonial settlements in the United States. A modern yet historic town with a population of just over 22,000, Guilford remains one of the most inviting and fascinating places to discover in Connecticut. Indeed, guests can explore several centuries' worth of history across an exploration of several landmarks that are included on the National Register of Historic Places. These include the Acadian House (1670), the Meeting House Hill Historic District, the Sabbathday House (1735), and the Medad Stone Tavern (1803), amongst others. In addition, outdoor lovers can also appreciate Guilford, and nice opportunities to go hiking, biking, and swimming at the nearby Metacomet Ridge are great ways to be immersed in nature. And do not forget about the Westwoods Trails, where caves, rock formations, and rolling streams make for some of the most unique hiking trails in all of Connecticut.

Also known as “The Constitution State,” Connecticut is one of the New England region's most fascinating and inviting places. With an incredible mix of historical intrigue and splendid natural beauty, Connecticut and its small towns are the very definitions of genuine Americana in a northeastern setting. From the historical setting of Guilford to the charming beach areas of Madison and Mystic, these and other inviting Connecticut towns are veritable treasures that all ages can enjoy and appreciate. So, when visiting New England, do not forget about Connecticut and its most welcoming towns. Here, a relaxing, informative, and charming vacation experience awaits all those with a desire to see authentic Americana!