Connecticut's 6 Unsung Small Towns

With its picturesque scenery and welcoming communities, this delightfully tiny state is always a refreshing escape from the hustle and bustle of city life to where old-world luxury meets modern charm. Whether you're escaping Hartford or NYC or skipping states to the shores of Long Island Sound, Connecticut's unsung small towns blend history and modernity, delivering the infamous New England charm in all its forms.

Along inviting Main Street and quaint trails, you'll stumble across art galleries, regal historic homes, and insightful museums near farms and wineries, and even a medieval-looking castle. Whether you're after historic chic, a seaside escape, or rustic nature ventures, these worldly towns know how to delight around the calendar with local talent and agriculture from Christmastime in Bethlehem to a beachy retreat in Old Saybrook.

Bethlehem

Knee-deep in the wilderness and agriculture of the Litchfield Hills, this charming New England town invites you to unwind from the city, celebrating the richness of the region with a blend of history and nature, family-style or with a group of friends. Many enjoy the generous March Farm, offering u-pick fruit and berries, a corn maze, plus farm-fresh treats and bucolic views. Minutes away, Hawk Ridge Winery is regionally renowned for its homemade wines, slushies, and scenic grounds.

Nature is never far at Bellamy-Ferriday House & Garden, where you can step back in time, exploring its period rooms, plus fascinating architecture and beautiful gardens on a stroll. Nonnewaug Falls is a moderate, dirt-trail hike to a stunning vale, particularly after rain. Art lovers enjoy the Abbey of Regina Laudis, a working monastery that houses a remarkable collection of crèches, including an 18th-century Neapolitan Nativity scene, when Bethlehem transforms into a real “Christmas Town.”

East Haddam

East Haddam has an idyllic feel along the east bank of the Connecticut River. Located amid notable attractions at the heart of the state, this classic NE town invites you to explore the intriguing beauty and history of the Connecticut River Valley, like the trails crisscrossing through the 860-acre Devil's Hopyard State Park, a rock-strewn forest, to the 60-foot Chapman Falls. In East Haddam, it is easy to fit in a tour of a modern medieval fortress and visit two neighboring towns, all on a single weekend.

The East Haddam Swing Bridge spans the river, carrying motor traffic plus a newly added pedestrian and cycling lane for a scenic pedal or stroll across to Chester. After browsing art by local artists, you can hop on the Chester/Hadlyme ferry back across the river, landing south of town by the enigmatic Gillette Castle, built by actor William Gillette on his estate in the early last century. Enjoy open park grounds daily and interior tours by appointment of the stone-faced mansion overlooking the river.

East Haven

Home to under 30,000, East Haven feels both cozy and spacious along an unsung shoreline of the Farm River as it tumbles into the Long Island Sound with various parks and beaches for relaxation and vitamin sea in exchange for the city hustle and bustle. The town's Shoreline Trolley Museum, the country's oldest in operation, features vintage exhibits and themed rides, while Lighthouse Point Park, a beachfront, is a prime spot among swimmers and birders with views of an 1847 lighthouse.

Besides the tidal river for brackish fishing and paddling, this scenic coastal slice encompasses the freshwater Lake Saltonstall with year-round fishing, trails, boat rentals, and an accessible pier. After exploring the marshy Farm River State Park, Sandpiper serves seafood and ice cream by the town's public beach, a family-friendly, serene spot with a splash pad, clean waters, and beautiful views. Whether you're shelling or taking a dip, the cool breeze and lapping waves have a soothing effect.

Essex

Boasting deep roots in shipbuilding and a fantastic, historic working waterfront of marinas, shipyards, and waterfront dining, this unsung harbor town is fun to explore for the whole family, and you can hop on for a narrated ride across the scenic Connecticut River Valley and a riverboat leg of the journey, a connection that is the only one of its kind in the US. Essex encompasses three charming villages with well-preserved early colonial and federal architecture, art venues, and river adventures.

Ivoryton flaunts the Ivoryton Playhouse, art galleries, and antique stores. Centerbrook, a revitalized factory hub on the Falls River, boasts adorable shops and is home to the famous Essex Steam Train. The waterfront Griswold Inn from 1776 offers to unwind in individually decorated, antique-filled rooms and colonial accents, just a 2-minute walk from the very kid-friendly Connecticut River Museum, housing shipbuilding history since the 18th century with art, artifacts, and model ships.

Kent

Snug along the New York border, Kent is both old-fashioned and avant-garde, with rustic nature that is a leaf peeper's dream, farm-to-fork eateries serving inventive dishes made from local ingredients, and art galleries. In addition to the easy Appalachian Trail access, the area's covered bridges warrant exploring through fall colors. Historic Bulls Covered Bridge is a popular stop south of Kent along a trail and the Housatonic River, which skirts the town under its Bridge Street—beautiful to drive across.

Minutes northwest, the 2,300-acre Macedonia Brook State Park offers fishing, camping, and hiking, with views of the Catskill and Taconic Mountains. Just up Hwy 7, the iconic Kent Falls State Park offers a hiking trail to a 250-foot waterfall, trout fishing, and picnicking. After a day out in nature, you'll be dying to unwind and recharge at one of the many spectacular restaurants or call it a night after dining at the top-rated Fife 'n Drum Restaurant & Inn across from SoDelicious HomeMade Bakery.

Old Saybrook

Old Saybrook, where the mighty and scenic Connecticut River tumbles into the Long Island Sound, inspires a relaxed waterfront retreat with shops and welcoming accommodations that stay open year-round, inviting an imminent visit to connect with the sea. Falltime is an ideal time with mature trees and bright foliage reflections in the water. Many come to imbibe the iconic Katharine Hepburn Cultural Arts Center, a historic theater and museum dedicated to Katharine Hepburn, a resident.

Down the festive Main Street, you can tour the 1767 General William Hart House near the triangular church green, ringed by regal, historic homes and churches, while the 17-acre Fort Saybrook Monument Park at the end of College Street offers storyboards on the historic Saybrook Colony, a boardwalk, and bird watching. From the grass-swept sands along Harveys Beach on the Sound to the rivermouth marina across, Saybrook Point Resort can be your dreamy oceanfront retreat.

There's something here just for you and special moments to embrace with your loved ones across CT's unsung small towns. The tiny state is home to Yale University, one of the eight prestigious Ivy League private schools in the Northeast, located in New Haven. Yale's precursor, the Collegiate School, was founded in Old Saybrook in 1701. Each welcoming, tight-knit community with a friendly nature on the doorstep shows how the best things come in small packages, especially surprises when you least expect them.