8 Most Hospitable Towns In Connecticut

Connecticut forms an important part of the northeastern region of New England, and the "Constitution State" has remained a place of wondrous allure from its days as one of the original Thirteen Colonies to the present. Admitted to the Union back in 1788, Connecticut’s beauty is indeed defined by both natural splendor and historic charm, and guests can expect to find a unique vacation experience here. Although the major cities like Hartford and Stamford still remain the best known, the smaller towns are often where a more intimate side of things is revealed. Friendly, hospitable, and darling communities fill the landscape. So, wait no more and come see the great state of Connecticut through a journey to these splendid towns.

Washington

Washington is a most charming historic community that can trace its roots to the 1770s. Home to nearly 3,700 inhabitants, the picturesque allure of this town, where natural beauty and historic intrigue come together, is certainly hard to beat. Visit three districts and truly get a sense of the 18th and 19th centuries through an exploration of multiple landmarks, many of which are also listed on the National Register of Historic Places. This includes the First Congregational Church, amongst others that feature Italianate, Georgian, and Greek Revival architectural styles.

From there, enjoy the outdoors, where warm and humid summers and cold winters are the norm. Spend time at Lake Waramaug or the Shepaug River, where swimming and boating remain ever popular. Meanwhile, with local businesses like Marty’s Cafe and The Hickory Stick Book Shop, a kind and welcoming atmosphere is never far away in this great Connecticut town.

Mystic

While going to the beach may not be the first thing to come to mind when thinking of Connecticut, the wonderful town of Mystic will surely change perceptions. Located along the state’s Atlantic coast, this historic community can trace its modern history to the 1780s. Once an important shipbuilding center, the historic charm of Mystic is evident, and guests can explore not one, but three districts dedicated to the town’s growth over several centuries. See preserved landmarks like the Clark Greenman House, and get a sense of life in the early days of America. And of course, one cannot forget about the Mystic Seaport Museum, founded in 1929. With interactive displays and an impressive collection of artifacts and other historic items, this incisive look into the region’s maritime past is indeed one of the finest cultural outings in Mystic.

Finally, the beach simply cannot be missed when in this town, and there is always a selection to choose from, including DuBois Beach, Williams Beach Park, and Esker Point Beach. With stunning coastal views, a pleasing and moderate year-round climate, and beachside businesses like the Oyster Club and the Olde Mistick Village, this is definitely one Connecticut community that warrants multiple visits.

Cornwall

Established in the 1740s and named for the English county, the historic town of Cornwall lies along the Housatonic River, with the stunning Berkshire Mountains acting as sentinels. Home to a modest population of just over 1,500 inhabitants, this community is a great place to enjoy a slower pace of life and relax in the outdoors. Known as the "greenest town in Connecticut," go fishing and boating along the aforementioned river, and hiking and biking trails also never disappoint. Meanwhile, do not forget about the nearby Mohawk State Forest, spanning some 4,000 acres.

Finally, for those looking to see some history, an exploration of the special covered bridges in the area is not to be missed. These include the West Cornwall Covered Bridge and many more that are also listed on the National Register of Historic Places. Other landmarks of note are the 1880s Cornwall Bridge station and the concrete Cornwall Bridge, completed in 1930. End the day with a meal at The Pink House restaurant, or simply stroll through Cornwall’s Main Street, and Americana Connecticut style will never be far away.

Guilford

Guilford is one of the oldest towns in the United States, with a history dating to the 1640s. Today, this fascinating, historic locale boasts a population of just over 22,000, and guests will not find a shortage of intrigue while visiting. Featuring centuries worth of stories, numerous preserved landmarks from the 17th, 18th, and 19th centuries continue to fascinate the public. Explore attractions like the Acadian House, Henry Whitfield State Museum, Hyland House Museum, and the Medad Stone Tavern Museum.

In addition, outdoor lovers can also appreciate Guilford's beach areas. These include Jacobs Beach and Chaffinch Island Park, where swimming, hiking, sailing, cycling, and picnicking are always popular. Add in local shops like Flutterby and the Prime on Whitfield restaurant, and it becomes clear why Guilford is a delightful place to visit.

Chaplin

The town of Chaplin was founded in the 1820s, and an inviting historic ambience is palpable. Guests can enjoy an intriguing sojourn accentuated by the area’s natural scenery. Begin with an exploration of the Historic District and marvel at its assortment of preserved 19th-century landmarks. These include the Congregational Church, Eaton’s Store, and the Witter House. Indeed, with architectural designs from Federalist to Greek Revival, the picturesque buildings here make for quite the photogenic outing.

Spend time at a number of pretty parks and green spaces, like Edward Garrison Park. Here, casual strolls, bike rides, local wildlife, and scenes of color-changing foliage make it a relaxing destination. Finally, start the day with a fine American meal at Blondie’s Country Diner, and get ready for an environment that showcases the state's friendly spirit.

Colebrook

Colebrook's origin story starts in the 1770s. An inviting place to spend a quiet and relaxing weekend, visitors to Colebrook can enjoy plenty of outdoor beauty. Visit the nearby Haystack Mountain Observation Tower for breathtaking panoramas, while opportunities to be active can be found at the Algonquin State Forest. Spanning almost 3,000 acres, activities like cycling, hiking, and wildlife watching are always popular here. And with its modest population of just over 1,300, the special feeling of small-town USA is never far away in Colebrook. Take in fun annual events like the Colebrook Holiday Fair and Colebrook Summer Fair, and see why this is such a lovely community full of local charm.

Westport

Westport is located about 48 miles from New York City in the southwestern corner of Connecticut. Founded in the 1830s and today the home of just over 27,000 residents, Westport continues to attract guests for its coastal views and beach areas perfect for all ages. Visit the Sherwood Island State Park for some of Connecticut’s best views, while beaches like Compo Beach and Old Mill Beach are the ideal places to go swimming, sailing, and sunbathing.

Westport’s historic character can also be experienced. Visit landmarks like the Bradley-Wheeler House and Shambaugh House. End the day with a stroll along the Saugatuck River, while a meal at Hudson Malone offers some American favorites in a casual and comfortable ambience.

East Lyme

Another beautiful coastal town, East Lyme is a great place to enjoy relaxing on the beach and taking in New England hospitality. Founded in the 1830s, this town continues to delight guests with its pleasing climate and scenic views. Spend time at a number of inviting beach areas, including Rocky Neck State Park, McCook Park & Beach, and the Hole-in-the-Wall Beach, and soak up loads of Atlantic sun, rocky shorelines, and soft sands.

In addition, one can explore several historic landmarks in town and the villages of Niantic and Flanders, creating a unique holiday experience. These include the Morton Freeman Plant Hunting Lodge, Samuel Smith House, and Smith-Harris House. Add in a fine meal at local businesses like Rossa Negra and Flanders Fish Market, and it becomes clear why East Lyme is one of Connecticut’s cutest gems.

Connecticut will please guests of all ages with its varied attractions and warm charm, which can be especially found in its smaller towns. From beachside coastal views to sites dating from the 1700s, there is never a lack of wonder to be discovered. Take in the port side character of Mystic, while the streets of Guilford will transport one back to the early days of colonial America. So, delay no more and come enjoy Connecticut by visiting these truly warm and welcoming towns.