9 of the Most Charming Towns in Connecticut
Connecticut is a small, quintessential New England state, packed with equally small towns at the backdrop of history, nature, and enviable cultures. These towns are incredibly beautiful, with their well-planned downtowns lined up with attractive homes and decorated with colorful trees. Walking through these communities is a satisfying experience, especially in the fall when the surrounding trees glow in picturesque glory.
As if that is not enough, natural endowments like the Connecticut River, scenic mountains, lakes, forests, and beaches also cut through or surround these towns, making them as charming as ever. Whether you are seeking to move to a place where the scenery alone is therapeutic or just looking to enjoy a typical New England vacation, these nine towns in Connecticut have you covered year-round.
Colebrook
Colebrook is a small town in Litchfield County with many outdoor charms waiting to be explored. First off, Algonquin State Forest is within the town and sets the stage for hiking, hunting, birdwatching, and fishing on Sandy Brook. In addition, the 700-acre Colebrook River Lake is another point of interest for fishing and boating, while its banks are perfect for relaxation and picnics.
In the heart of the town, the Colebrook General Store (built in 1812) invites visitors to marvel at its collections and long business history. Afterward, chill at the Norbrook Farm Brewery over beer and food from a truck.
Essex
Essex is a delightful river town in Middlesex County with something to offer every traveler, from history buffs to adventurers. Once here, one can start by experiencing the Essex Steam Train and Riverboat tours, which wind through the captivating landscapes of the Lower Connecticut River valley down to Haddam Swing Bridge.
Afterward, history enthusiasts can head to the Connecticut River Museum to learn about the iconic river and its role in the development of several towns, including Essex. After exploring, relax at Essex Park with views of the river or stroll around. For sensational dining experiences, visit Scotch Plains Tavern and admire contemporary artworks at Copper & Smith Gallery.
Chester
Chester is a quaint town in the Lower Connecticut River valley in Middlesex County, capable of stealing the hearts of visitors just with its natural scenery, but there is more. Once here, fans of history can discover and learn about the faded era of the town and its early roots at Chester Museum at the Mill, featuring exhibits and two millstone artifacts. On the outdoors, this town invites adventurers to ride the Chester-Hadlyme Ferry, linking the towns of Chester and Hadlyme over the Connecticut River. When the ferry gets to Hadlyme, don’t return without touring the Gillette Castle State Park, which hosts a magnificent castle above the Connecticut River, built by William Gillette in 1914.
For more adventures, head to Cedar Lake in Chester to enjoy dips in the 50,000-square-foot swimming area and picnic on the banks. Elsewhere, art lovers can check out the Lori Warner Studio/Gallery to see awe-inspiring paintings and proceed to the 200-seater Terris Theater for entertainment.
Madison
Madison has its fair share of picturesque shorelines along the Long Island Sound while flaunting a rich historic allure. As a waterfront town, its beaches are highlight attractions, starting with the Hammonasset Beach State Park, home to the longest public beach in the state. Other top beaches in town include East and West Wharf and Surf Club Beaches, all offering thrilling beach activities from water sports and picnicking to camping, swimming, fishing, and sunbathing.
Hikers and bikers can hit the Shoreline Greenway Trail, to enjoy mesmerizing coastal views along forested paths. History fans can proceed with a tour of the Madison Green Historic District to see ancient structures such as Deacon John Grave House (1681) and First Congregational Church of Madison (1838). Relax at the Madison Cinemas to appreciate mainstream and blockbuster movies, and savor Italian Mediterranean cuisines at Café Allegre afterward.
Old Saybrook
Old Saybrook is a dazzling small town along the Connecticut River, brimming with history, culture, and stunning scenery. On a trip here, visit Harveys Beach overlooking Long Island Sound to build sand castles, sunbathe, enjoy picnics, play, swim, and fish on the water. Boat cruise or kayak down the river to see Lynde Point Lighthouse, which has guided ships from the Connecticut River to the Sound for centuries.
Plug into history at the Fort Saybrook Monument Park along the river and take history lessons through informational signs that offer a glimpse into the town's origin. For more history, head to the General William Hart House (c. 1767) to see memorabilia from bygone eras and also explore a historic garden. Before leaving town, shop for antiques as souvenirs at Maximus Antiques.
Westport
Westport is an adorable town along the Long Island Sound with a blend of history, arts, culture, and outdoor sensations. Once here, start by visiting the Museum of Contemporary Art (MoCA) to explore its rich collection of modern artworks and galleries. Next, delve into history at the Westport Museum for History and Culture, where the town's past resonates through various exhibits and relics. Take things a step further by visiting the 235-acre Sherwood Island State Park on the Long Island Sound to stroll, watch birds, or hold a picnic on the beach and take pictures at the backdrop of its September 11 memorial.
Other beaches for swimming, sunbathing, picnicking, and promenading in Westport include Compo and Burying Hill beaches, while the Saugatuck River beckons for paddling and kayaking. Those hungry for entertainment can proceed to Westport Country Playhouse, a historic theatre that offers Broadway-like shows. Don’t forget to dine at Westport Bartaco or Rainbow Thai while in town.
Mystic
Mystic is a historic town in Connecticut, renowned for its seaport museum and the largest maritime museum in the US. History buffs would love this museum as it is home to four National Historic Landmark vessels, including the country's oldest whaleship, Charles W. Morgan, constructed in 1841. In addition, the museum has a harbor, restaurants, a planetarium, and boats to sail on the water. Visitors can proceed to admire the Mystic River Bascule Bridge over its namesake river, and head to the Mystic Museum of Art afterward to see historic American artworks and dynamic galleries.
Away from history, boat on the charming Mystic River and bask on the sands of Williams Beach Park. Don’t miss a visit to the Mystic Aquarium, where one can spot Beluga Whales and even touch the wings of Rays and Sharks. When it's time to wine and dine, check out AJ’s Bistro on the waterfront or the Oyster Club.
Branford
Branford is a small town offering an escape from the heat and bustle of nearby New Haven. With the town being close to water bodies like Lake Saltonstall and Long Island Sound, opportunities for water-based recreation are endless. Additionally, the town is home to beaches such as Branford Point, Stony Creek, Short, Sunset, and Front Beaches, where visitors can sunbathe, swim, promenade, hold picnics, and build sand castles.
Meanwhile, a boat cruise to the Thimble Islands could be the highlight of a visit to this town, as more activities like fishing and kayaking await. For history buffs, Harrison House Museum is a perfect destination to explore the past via various tools, artifacts, exhibits, and photography. Before leaving town, head to Legacy Theatre to enjoy shows and events, and don’t forget to relish the taste of Ashley’s Ice Cream.
Kent
Kent is, without a doubt, one of the most enchanting towns in New England. It is sliced by the Housatonic River and overlooked by the Appalachian Mountains. For a satisfying experience here, start by visiting Kent Falls State Park to hike, admire several gorgeous waterfalls, and fish in streams stocked with trout. Next, explore the Macedonia Brook State Park to hike its network of trails, enjoy picnics, and admire the brook and a small hilltop lake. Still, on the outdoors, check out the iconic Bulls Covered Bridge, one of the few covered bridges in the state. History buffs can visit the Eric Sloane Museum to see ancient hand tools alongside the remains of the Kent Iron Furnace. When hungry, head to the Villager Restaurant and Catering or Fife ‘n Drum Restaurant to savor various culinary delights.
Visit the charming small towns of Connecticut to experience life in scenic landscapes where time seems to move slowly and outdoor experiences hit differently. From adventures and cultural immersions to hopping historic attractions, there are plenty of things to do and see in these towns. Come with a camera because the sights will be wondrous and an explorative spirit to seek out hidden gems. These towns are also perfect for weekend retreats, summer vacations, and day trips to get away from it all.
