These 9 Towns Are Connecticut's Best-Kept Secret
Connecticut isn't just a pit stop between New York City and Boston; it's a U.S. state full of towns that quietly steal the spotlight. At least, if you know they exist. In these nine places, winding streets reveal indie coffee shops, hidden riverside hangouts, and art studios brimming with creativity. Some nudge you to linger over a lakeside patio, others tempt you to wander through history tucked into quiet neighborhoods. While each of these Connecticut towns has its own distinct personality, they all share one thing: they're underrated, overlooked, and, quite frankly, some of the state's best-kept secrets, waiting for anyone curious enough to discover them.
Mystic
Too few people know about the Julia Roberts film Mystic Pizza, let alone the town it was based on. Yes, in the southeast Connecticut town of Mystic, there is, in fact, an actual Mystic Pizza. It sits along Main Street, which buzzes with restaurants and pubs, not to mention Mystic Drawbridge Ice Cream, a local standby that's as much about people-watching the river traffic as it is about ice cream. The ice cream shop is perched at the entrance of the Mystic River Bascule Bridge, which lifts for passing boats floating down the Mystic River. While the whole place feels like it was ripped straight out of a movie, including all of the nods to its maritime past, there are still natural attractions that you can get lost amongst. This includes the nearby Peace Sanctuary, a nature preserve with scenic trails and river views.
Chester
Chester, tucked into the Connecticut River Valley, feels like a discovery only insiders know. Main Street teems with colorful storefronts, cafes, and local galleries. We have to emphasize the latter, as those who know about Chester are aware of its quirkiness and flair for the creative. Both Lori Warner Studio/Gallery and Leif Nilsson Spring Street Studio embody this. Music also threads through the town with the annual Robbie Collomore Concert Series filling the historic Chester Meeting House with jazz, classical, and roots performances. Chester is also home to one of the country's oldest continuously operating ferries, the Chester-Hadlyme, which takes you across the river from Chester to the town of Hadlyme. And a short drive away is Mount Pisgah, a modest but gorgeous summit you can climb before heading back into town for a drink at the River Tavern.
Essex
Downriver from Hartford, the town of Essex sits on a bend of the Connecticut River and is one of the state's best-kept secrets. The streets lean old New England with flagstone walks, clapboard houses, and storefronts that haven't lost their character to time. Down by the water, the Essex Steam Train still exhales smoke like it did a hundred years ago, and takes you through to surrounding Connecticut towns that deserve nearly as much attention as this place. Back in town, locals might tell you that the real gem is the taproom at The Griswold Inn, where live music spills out beneath beams darkened by nearly 250 years of use. The river town curves around three coves, South Cove, Middle Cove, and North Cove, each of which has access points where you can launch boats and kayaks into the Connecticut River and get a completely different vantage point of the historic town.
Stonington
Tucked on a slim peninsula between Fisher's Island Sound and Little Narragansett Bay, Stonington is the kind of place even lifelong New Englanders sometimes miss. Water Street's brick storefronts and weathered captains' houses feel unchanged in decades, and you can still hear the clatter of halyards from the harbor at the end of the block. This is also where you'll find some of the best restaurants in town, including Dog Watch Cafe. DuBois Beach, small and sandy, looks straight across to Rhode Island, while the 1840s Harbor Light rises just behind it, a stone tower with steps leading to a lookout above the bay. Slip east and you'll find Barn Island, where five miles of trails cut through salt marsh and tidal flats, a haven for herons and egrets.
Litchfield
Litchfield sits amid rolling hills in northwest Connecticut, a town that manages to feel discovered and undiscovered at the same time. The Tapping Reeve House and Law School lets you step into early American legal education, complete with original classrooms and a meadow where students once debated cases. Downtown, the town green is lined with 18th-and 19th-century homes and a handful of precise, well-curated shops and restaurants, such as The Village Restaurant and Market Place Tavern. Litchfield Distillery, just a few blocks off the green, takes local grains and turns them into bourbon, gin, and whiskey, with tours and tastings offered daily. Outside town, the White Memorial Conservation Center stretches across 4,000 acres, with wetlands, forested trails, and the Little Pond boardwalk, which offers close-up views of beavers, foxes, and migratory birds.
Cornwall
Cornwall was incorporated in 1740 and contains three distinct areas (or townships): West Cornwall, Cornwall Bridge, and Cornwall Village. The West Cornwall Covered Bridge, built in 1864, is still open to traffic and cuts a wooden line over the river. Near the bridge, you can grab a bite to eat at the swanky Pink House restaurant. Federal-style homes line the streets of Downtown Cornwall, and a few shops with the Cornwall Historical Society anchor the village and offer insight into the town's colonial and Revolutionary-era history. This underappreciated town is also a gateway to Mohawk Mountain, a haven for skiers. But it's not just for those who love barreling down a snowy mountain; it's Cathedral Pines trail winds through some of New England's oldest preserved white pines, opening onto the summit that, on clear days, reveals the Berkshires, Catskills, and even Mount Greylock.
Washington
If Stars Hollow were real, it would be Washington Depot, a village inside the Connecticut town of Washington. The creators of Gilmore Girls have claimed that their fictional town was directly inspired by this relatively unknown spot. Walking into Washington Depot, it's hard not to imagine Rory and Lorelai strolling the green. The town's village center hits the same mix of quirks and intimacy: the century-old Washington Food Market nods to Doose's, while Marty's Cafe hums with the neighborhood energy of Luke's Diner. There are even antique shops like Five Janes and a hardware store to complete the connection to the show. Just beyond the village, Lake Waramaug stretches across 656 acres and is a perfect place for canoeing or kayaking. Hollister House Garden rises on a nearby hillside, its sculpted hedges and wildflower beds opening onto meadows that feel like they were plucked from a small-town sitcom set. On top of all of this, Washington is home to some truly fantastic spas, such as the Mayflower Inn & Spa.
Winsted
At the heart of Winchester, Connecticut, is the town of Winsted. Main Street feels cinematic with Victorian facades, neoclassical churches, and a mix of quirky shops like LiVe.AtHome and Cura Di Se, which give the streets a 'lived-in', small-town energy. In Winsted, art is everywhere. Whiting Mills, a repurposed hosiery factory, hosts over 50 artists' studios, while the nearby American Mural Project fills a five-story wall with a tribute to American workers. Beyond the village, Highland Lake sprawls over 506 acres, drawing swimmers and boaters in the summertime. It's one of the largest lakes in the state and is known for its crystal-clear water. This hidden gem of a town is also home to The Soldier's Monument and Memorial Park, a Gothic Revival tower that rises above the treeline and honors local soldiers who served during the Civil War.
Kent
Kent Falls State Park is undeniably the centrepiece of the town of Kent. It's Connecticut's tallest waterfall and tumbles roughly 250 feet in a series of drops. You can see the falls right from the parking area or take a stroll to the base. For a more immersive experience, stairways alongside the cascade lead to multiple viewing platforms. Downtown Kent delivers a concentrated dose of the town's quiet and underappreciated character. Main Street consists of a series of restored barns and old houses now home to local businesses like Woodford's General Store, House of Books, and Heron Shop. The architecture, paired with tree-lined streets and glimpses of nearby hills, keeps the center feeling both historic and insanely welcoming. The town sits on the northwest edge of Connecticut along the New York border, quietly holding its spot as one of the state's lesser-known treasures, even with the undeniably beautiful Macedonia Brook State Park spreading across 2,300 acres mere minutes from downtown.
Connecticut's lesser-known towns are where the real discoveries happen. Mystic keeps you guessing with its riverside allure, Kent drops jaws with waterfalls and forested trails, Cornwall charms with art, and Washington draws some pretty impressive parallels to Gilmore Girls. These are not towns everyone posts about; they're for those who love discovering quiet, tucked-away spots free from crowds and Instagrammers. Connecticut's best-kept secret towns are calling, and they're worth every detour.
