10 Most Breathtaking Towns In Connecticut

Connecticut concentrates much of its most breathtaking scenery in two very different corners of the state, namely the Long Island Sound shoreline and the Litchfield Hills of the northwest. Kent Falls descends a cumulative 250 feet through Kent Falls State Park before Falls Brook empties into the Housatonic River. A 172-foot lattice-truss covered bridge has carried traffic over that same river at West Cornwall since about 1864. Along the coast, the Charles W. Morgan sits at Mystic Seaport Museum as the last wooden whaleship left in the world. In these ten Connecticut towns, the state's most noteworthy views usually come with a story attached.

Mystic

Mystic is a popular summertime destination thanks to its compact, easily navigable downtown. Trove, on West Main Street, specializes in men's fashion and gifts. A few blocks away, Oyster Club serves locally sourced New England seafood in a casual but elegant space. The Captain Daniel Packer Inne shines late into the evening with specialty cocktails and live music several nights a week, inside a building constructed in 1756.

Mystic also preserves its rich maritime history at the Mystic Seaport Museum, a collection of historic ships and merchants' vessels accompanied by an immersive recreation of a 19th-century village. Docked right outside on the Mystic River is the Charles W. Morgan, the last wooden whaleship left in the world and now open for tours.

Kent

Kent pairs its natural attractions with a shopping and dining strip on North Main Street. Kent Falls State Park contains a number of trails centered on Kent Falls, a series of cascades that descend a cumulative 250 feet along Falls Brook over roughly a quarter mile, making it the tallest waterfall in the state by total drop. No single plunge in the sequence exceeds about 70 feet. A more challenging hike can be found at Macedonia Brook State Park, where the Macedonia Ridge Trail crosses Cobble Mountain for views of the Catskill and Taconic Mountains.

Kent Falls Brewing Company operates out of a restored dairy farm on Camps Road, with a small indoor taproom and a much larger outdoor patio. Fife 'n Drum Restaurant & Inn has been a fixture on North Main Street for decades, and its dining room is known for tableside preparations and a deep wine list.

Essex

Located on the banks of the Connecticut River, Essex offers a brilliant blend of nature and history. The Essex Town Green is an immaculately landscaped park at the center of the village. The Pratt House on West Avenue stands nearby, its oldest sections dating to 1701. So does the First Baptist Church of Essex. Dating to 1846 and modeled on a Minard Lafever design, it is one of only three Egyptian Revival churches ever constructed in the United States.

Meanwhile, the Essex Steam Train takes passengers on a 2.5-hour journey through the Connecticut River Valley in a restored 19th-century locomotive while a conductor points out important historic sites along the way. The Connecticut River Museum chronicles the region's shipbuilding heritage through exhibits, artifacts, and vessels, including a full-scale reproduction of the Turtle, the world's first submersible with a documented record of combat use.

Westport

Westport is an affluent coastal community known for its beaches and high-end shops. Visitors typically devote a good deal of their time to Compo Beach, which extends along the Long Island Sound near the mouth of the Saugatuck River. Just a few miles east lies Sherwood Island State Park, 238 acres of sandy beach, dunes, meadows, and coastal woodland. State land purchases here began in 1914, which makes Sherwood Island the first state park in Connecticut. Like its boutiques, Westport's dining scene skews upmarket. The Whelk, on Riverside Avenue, is known for its seafood menu and an outdoor area with Adirondack chairs and fire pits. Nômade on Main Street is one of the newer additions, with a seasonal menu that borrows from several European and South American traditions.

Cornwall

Set in the southern Berkshires, Cornwall is a haven for outdoor enthusiasts. The Pine Knob Loop Trail winds through the white pines and hemlocks of Housatonic State Forest and coincides with the Appalachian Trail for part of its length, opening onto vistas over the Housatonic River valley. More experienced hikers typically gravitate to 1,683-foot Mohawk Mountain, the high point of the blue-blazed Mattatuck Trail. Its summit takes in the Taconic and Berkshire ranges, with the eastern Catskills visible on a clear day. Cornwall's relationship with the landscape shows up again in the West Cornwall Covered Bridge, a 172-foot red spruce lattice truss completed around 1864 that still carries Route 128 across the river.

Dinner in the village of West Cornwall often means RSVP on Railroad Street. The tiny French restaurant serves a multi-course chef's menu on weekend evenings. The Wish House, a short way up the Sharon-Goshen Turnpike, stocks clothing, toys, housewares, and artwork. It also hosts a small farmers market on Saturday mornings through the warmer months.

Madison

Madison is home to Hammonasset Beach State Park, the largest shoreline park in Connecticut and a major hub for swimming, biking, surfing, and boardwalk strolling. Its two miles of sand make up the longest public beach in the state. The town also has its own Surf Club Beach, with roughly 1,200 feet of shorefront, a boardwalk, and open views of the Long Island Sound.

Inland, Rockland Preserve covers some 650 acres of rounded rocky hills, gray ledges, and abandoned colonial roads, with Coan Pond as its centerpiece. On Boston Post Road in the town center, Susan Powell Fine Art shows paintings and photography by more than 50 artists. Back at the shore, The Wharf Restaurant occupies the ground floor of the Madison Beach Hotel on West Wharf Road, with a terrace over the water.

Chester

Chester's downtown center may be small, but it carries an unusual amount of culture for a village of its size. Three Fates on North Main Street serves coffee in the morning and cocktails at night. The galleries sit within a few hundred yards of one another. Leif Nilsson Spring Street Studio and Gallery hosts a summer concert series in its garden. Lori Warner Studio is on Main Street, and the aptly named Chester Gallery doubles as a frame shop. The Wheatmarket on Water Street is the go-to sandwich shop, though its soups deserve equal billing.

Local residents can often be seen getting their exercise at Cockaponset State Forest, the second-largest state forest in Connecticut. Popular trails include the West Woods Loop, which climbs to elevated views of Lost Lake. For dinner, Grano Arso is a seasonal Italian restaurant set inside the former Chester Savings Bank building of 1902, where chef Joel Gargano mills New England grains in-house for the breads and pasta.

Old Saybrook

Old Saybrook sits where the Connecticut River meets the Long Island Sound, and its beachfront stays quieter than the state parks to the west. Harvey's Beach, the town beach on Great Hammock Road, has soft sand, gentle water, and a sandbar that emerges at low tide. Main Street is worth a wander any time of day. Penny Lane Pub does British pub food under a wall of Beatles memorabilia, while Sip Wine Bar serves flights and monthly wine classes, with bottles from Italy, France, and Hungary.

Old Saybrook is also famous for its historic lighthouses. Lynde Point Lighthouse dates to 1838, and the Saybrook Breakwater Lighthouse to 1886. Neither is open for tours, but both are visible from the water on a Seabird cruise. The boat departs from Saybrook Point Marina for sightseeing and sunset trips on the Connecticut River.

Willimantic

History comes to life in Willimantic, known as Thread City because it was once home to several major textile mills of the American Thread Company. Fans of Victorian architecture will be in heaven at Willimantic's Prospect Hill district, dotted with well-preserved 19th and early 20th-century homes. The Windham Textile and History Museum on Main Street fills three floors with antique sewing machines, Victorian furniture, and recreations of mill worker housing.

Just a short walk away lies the Garden on the Bridge, a planted span above the Willimantic River with benches facing a double set of falls and the old mill buildings beyond. Farther down Main Street, Willimantic Brewing Company serves a wide range of house beers and American food inside a former United States post office, high ceilings and all.

Colebrook

A town of fewer than 1,400 people, Colebrook sits in the Litchfield Hills, one of the most visually captivating areas of the state. Algonquin State Forest covers a large share of its land, though most residents and visitors prefer to do their hiking at Colebrook River Lake, a reservoir popular for fishing and kayaking. Norbrook Farm Brewery adds several miles of its own trails across roughly 450 acres of hill farmland, along with a taproom, a disc golf course, and farm animals for the kids.

Colebrook's scenery is also complemented by a notable concentration of historic buildings. The Greek Revival Colebrook Congregational Church went up in 1842, and the Samuel Rockwell House at the north end of the green is dated by local records to the second half of the eighteenth century. The Colebrook Store, built in 1812 and listed on the National Register of Historic Places, held the title of the oldest continuously operated general store in Connecticut until 2007. It has been closed since late 2024, and a local preservation group is working to bring it back.

Connecticut's Two Kinds Of Beauty

Connecticut's beauty divides along the same line the whole way down the state, with the Connecticut River valley and the Long Island Sound shoreline holding as much scenery as the Litchfield Hills. Essex has its Town Green on one side and the river on the other. Hammonasset Beach State Park gives Madison the largest shoreline park in the state, and two nineteenth-century lighthouses stand at the river mouth in Old Saybrook. In all ten of these towns, the scenery alone is worth the trip.