2025's Most Underrated Towns In Connecticut
More people seek quieter, yet vibrant, escapes. Welcome to the state that invented Main Street America. The Constitution State's natural beauty is wildly underrated, while the sheer amount of town greens wrapping around colonial architecture is worth a themed trip. The nation's first law school was founded in 1784 in Litchfield, while Simsbury is surrounded by some of the state's tallest peaks.
Talcott Mountain State Park features a 950-foot-high promontory with unparalleled vistas into New Hampshire. Stonington, one of the coastal delights, is next to Mystic, which is the enclave that semi-accurately portrays the social caste in Mystic Pizza. Some associate the Long Island Sound with the likes of New York's Hamptons. Discover Connecticut's "side of the story" in the first town.
Guilford
Just 24 minutes east of New Haven, Guilford's intricate blend of natural beauty and historic architecture makes it a haven for sightseers. Chaffinch Island Park features picnic tables and grills with unobscured views of the sweeping Sound. Take a dip from the small jetty on a hot summer afternoon. Chittenden Park is the southern end of the New England Trail, while Jacobs Beach is one of the best in Connecticut. Guilford Green features a colonial collection of homes, local shops, and eateries. Drop by Cilantro Specialty Foods for a sandwich and coffee to go on a verdant stroll.
The 17th-century Henry Whitfield State Museum in the state's oldest stone house transports you to colonial life on a tour. Don't miss Breakwater Books and the Village Chocolatier. The surrounding shoreline calls for a bike ride. Guilford Sea Nook offers to capture how well the mid-century modern architecture is integrated on the coast. Across the marina, Grass Island is rarely crowded to explore in its peaceful ambiance and relax, anticipating a crazy sunset. Falkner Island Light is visible on the small island quite a way offshore amid a reef.
Litchfield
Litchfield exudes quaint charm over the rolling hills in northwestern Connecticut. The nation's first private law school was founded here by Tapping Reeve in 1784. Although closed in 1833, it cemented Litchfield's identity as a legal education hub in the US. Drop by Tapping Reeve House and Law School. Litchfield draws crowds with colonial architecture preserved at the Litchfield Green. Browse antique stores and Aloft Gallery, then relax "@ the Corner," serving new American flair. Others know of the immense hiking and wildlife watching through the Litchfield Hills.
Just south, the Little Pond Boardwalk Trail loops under two miles through marsh and woods with beautiful views and different birds. There's also the crowd-free Litchfield Town Beach on Bantam Lake. Mount Tom State Park is one of the most underrated in Connecticut, while Wyantenock State Forest is a rugged, dreamy preserve for hiking and biking through 4,000 largely undeveloped acres. Under 30 minutes west, Kent Falls State Park features the eponymous 250-foot waterfall along a trail for a hike with a picnic, plus trout fishing.
New Canaan
Before this idyll got connected via an offshoot metro line to NYC, New Canaan was overlooked for Norwalk. Being under 10 miles from the coast, it makes for an uncrowded base, rich in vegetation through gardens and preserves. From the station on Elm, walk just a block for the good vibes and local boutiques at the shopping village, plus branded delicacies, Spiga for Italian, and a picturesque playhouse. Roger Sherman Inn is a sought-after stay downtown in a classic 18th-century home. Explore the Nature Center's 40-acre sanctuary of meadows, woodlands, ponds, and marshes.
New Canaan Museum & Historical Society showcases various exhibitions, while Waveny Park calls to relax after shopping, perhaps with a treat from the Gelatissimo Artisan Gelato—relevant, snow or shine. Ditto the historic Philip Johnson’s Glass House, a midcentury modernist masterpiece with seasonal tours, a garden, and a cafe. Minutes north at the state border, the 80-acre Grace Farms is a design destination. Kazuyo Sejima and Ryue Nishizawa designed its anchoring cultural hub, River Building. There is a nearby wildlife trail and a pavilion for tea. Drive to the coast at sunset.
New Hartford
New Hartford is an obscure gem for nature lovers in the river valley in the state's northwest corner. Stricken through the heart by the Farmington River and the imposing south shore of Lake McDonough, there's no off-switch to this outdoorsy town, truly. Explore the verdant summertime valley and the riverfront downtown, browsing quaint shops and relaxing patios for a drink. Farmington River Tubing is a popular service for a thrilling ride, and Main Stream Canoes & Kayaks/SUP offers rentals for confident water enthusiasts.
Find Barkhamsted Reservoir to the north past the first lake. No visit is complete without this picturesque drive, which can only be described as a postcard-perfect shot of Northern Connecticut. Get out for a stroll along the panoramic highway to a picnic spot with a magnificent view. In the spring, fly fishermen hound around one of the state's most famous catch-and-release areas. Vibrant foliage carpets the rolling hills in the fall, while Collinsville Antiques Co. is worth the drive alone. The local winter slopes offer trails for all skill levels.
Norfolk
Berkshires bless the towns in the foothills with views and fresh air. Norfolk has an extroverted personality with its own monthly newspaper and an acclaimed library. There is the Music Shed, a pub, and a thriving farmers market, plus the Connecticut-Asia Cultural Center, minutes down the road. Drop by the gorgeous historical museum to travel back to its establishment in 1758. The historic, 300-seater Infinity Music Hall flaunts a proscenium stage for music shows and a bistro in 1883 digs, while a number of fine inns and restaurants offer to unwind and recharge for the boundless outdoors.
This particularly picturesque rural town feels lost at the border with Massachusetts. Campbell Falls State Park, Dennis Hill State Park, and Haystack Mountain State Park surround Norfolk with adventures for every level and taste. The latter is a beloved hiking spot for families, breathtaking in the fall, with top views of 360 degrees around from the historic tower of the mountainous panorama. There are also three scenic lakes to the northeast, like the charming Doolittle Lake. Wood Creek Pond is never crowded with a boat launch and few others, just wildlife to disturb your peaceful paddle.
Simsbury
One of the few to offer a free rental bike program, this historic Farmington Valley town is a haven for cyclists. Gear up at various stores for a ride along Iron Horse Blvd and the Farmington Canal Heritage Trail. Miles of paths and walking trails connect the most popular attractions. Simsbury Meadows Performing Arts Center hosts the Hartford Symphony in the summer, while the 19th-century Old Drake Hill Flower Bridge feels integrated into the river views. After all that pedaling, the quirky Plan B Burger Bar serves inventive burgers, elevated grub, craft beers, and bourbons.
Surrounded by craggy peaks and forested slopes, the area lights up in fall foliage. Simsbury boasts proximity to the infamously beautiful view at the Talcott Mountain State Park, with wildlife to spot atop the 165-foot tower. Minutes west, Stratton Brook State Park features a red-covered bridge, while Penwood State Park offers a wooded trail system, lakeside paths, and picnic areas across the Farmington River east. Tee off at Wintonbury Hills Golf Course, and when it's time to recharge, Abigail's Grille and Wine Bar is a Colonial-era tavern with a patio and cozy dining room.
Stonington
Lost in the sea of other towns, Stonington has an elevated feel on its very own peninsula along the state's craggy shore. Explore the harborfront to Stonington Point next to Dubois Beach, with gentle waves for swimming, an anchored dock, and a jetty for crabbing. Water Street, the main artery, features quaint shops, while Dodge Paddock/Beal Preserve offers a chance to get away from it all in a serene spot. Book the retro-style New England Inn, and visit Saltwater Farm Vineyard just northeast for a stroll along the vines and relaxation with a glass in a very scenic place.
Mystic is actually a census-designated village, while Stonington is Mystic’s eastern half. Among hotspots, Dog Watch Cafe is a relaxed seafood and BBQ joint with outdoor seating and lawn games. Between living on the high, get some activity in at the 1,013-acre Barn Island Wildlife Management Area, like bird-watching, hiking, and fishing. The inland Velvet Mill is a great indoor farmers market to dine on-site with a brewery and distillery, plus stock up on souvenirs through local boutiques and vintage shops. Don't miss the seasonal Captain Nathaniel B. Palmer House Museum.
Washington
Boasting a high concentration of colonial architecture, finding this town away from big cities means irrevocably falling for its charms. The producers of Gilmore Girls did since the spirited, tight-knit Stars Hollow is widely regarded to be based in Washington. The charming smattering of brick-and-mortar is like eye candy to the soul, with places to eat and drink local to your heart’s content. Steeped in the wilderness of western Connecticut, Steep Rock Preserve is drenched in serenity, with trails for hiking, biking, and horseback riding past a cool train tunnel and suspended bridge.
Hidden Valley Preserve has a magic allure across the suspension bridge every season. It is easy to see the source of inspiration in rural Litchfield County, particularly through the Washington Green Historic District. Visit nearby wineries, like the iconic Hopkins Vineyard on the north shore of Lake Waramaug. From Warren Town Beach, it is just 13 minutes south to Washington. From Marty's Cafe and the next-door Eckert Fine Art to the white church steeple visible from the window of Po Cafe on a green lawn, browse Hickory Stick Bookshop for a new read and memory of town.
Embracing Connecticut's Lesser-Known Treasures
Connecticut's charming blend of coastal towns, lush countryside, and deep wilderness areas offers an easygoing getaway. Unlike the neighboring Rhode Island or Massachusetts, this New England state's carefree trait is possibly an extension from New York to the West. No description does the state justice whose beauty is unparalleled.
From the Farmington River Valley to the Berkshires, choose a town for an easygoing getaway to be reminded of life's simple pleasures. Under the radar, off the beaten path, call it what you will. The "underdogs" offer a taste of authentic NE life. No longer standing to be overlooked, these eight quieter yet vibrant towns must be on your radar in 2025.
