14 Most Beautiful Small Towns In Connecticut You Should Visit
Bordered by Rhode Island, Massachusetts, New York, and Long Island Sound on its east, north, west, and south, respectively, Connecticut is the southernmost state in the New England region of the American Northeast. Being one of the original Thirteen Colonies and featuring picturesque sandy beaches, harbors, rolling forested hills, sparkling waterbodies, and village greens encircled by colonial structures, Connecticut represents a perfect amalgamation of historic sites, rural landscapes, and modern urban life. Dotting the nation’s third-smallest state by area are numerous adorable small towns, each with stunning natural sceneries, rich history, vibrant cultures, many outdoor recreations, and restaurants serving delectable cuisines. So, whether you want to enjoy a quick weekend getaway or an extended vacation, these small towns in the Nutmeg State will not disappoint.
Mystic
Named after the native Pequot term “missi-tuk,” which refers to a “great tidal river,” this historic resort village and census-designated place is located along the Mystic River shores in Groton and Stonington towns of New London County. Mystic, a significant New England tourist destination, contains three historic districts: the Mystic Bridge Historic District, the Rossie Velvet Mill Historic District, and the Mystic River Historic District. Visitors to Mystic must take a tour of the Mystic Seaport Museum, one of the world’s premier and the country’s leading maritime museums, and witness the historic vessels, more than 500 historic watercraft, maritime art gallery, research library, and a recreated 19th-century seafaring village. Tourists can also visit the Mystic Aquarium & Institute for Exploration and the Mystic Museum of Art or enjoy a scenic cruise down the Mystic River. Lining the business district on either side of the Mystic River Bascule Bridge are several gift shops, galleries, cafes, bakeries, and restaurants serving tasty seafood and special Mystic Pizza for travelers.
Chester
A small rural town in south-central Connecticut’s Middlesex County, Chester, is part of the Lower Connecticut River Valley Planning Region. Initially a New England mill town and shipbuilding community, Chester honors its rich heritage besides offering colorful cultures and modern-day amenities. The town’s winding Main Street is lined with meticulously preserved colonial-era structures that house an array of shops, boutiques, art galleries, and award-winning restaurants. Travelers are drawn to Chester’s many noteworthy attractions like the Old Town Hall, Charles Daniels House, Jonathan Warner House, Villa Bella Vista, Dr. Ambrose Pratt House, Beth Shalom Rodfe Zedek synagogue, Chester Museum at the Mill, and the acclaimed Goodspeed Opera House – Norma Terris Theatre. Outdoor enthusiasts would love to take a scenic walk at the Cockaponset State Forest, visit the Chakana Sky Alpacas farm, camp at Camp Hazen YMCA, or enjoy a ride on the Chester-Hadlyme Ferry, the state’s second oldest continuously operating ferry service.
Old Saybrook
One of the state’s oldest and most beautiful towns, Old Saybrook is located in Middlesex County, where the Connecticut River meets the Long Island Sound. As the Lower Connecticut River Valley’s retail, commercial, and small manufacturing hub, Old Saybrook actively promotes the area’s economic and business development. The town’s thriving Main Street contains scores of retail establishments offering innumerable shopping options and gastronomic experiences. Visitors can tour the town’s many historic structures, including Black Horse Tavern, Connecticut Valley Railroad Roundhouse & Turntable Site, Lynde Point Lighthouse, John Whittlesey Jr. House, Saybrook Breakwater Lighthouse, etc. They can also watch a play at the Katherine Hepburn Cultural Arts Center, enjoy the tranquil sandy beaches, and explore the hiking trails and traditional walking paths at the Great Cedars Conservation Area and the Gardiner’s Landing & Fort Saybrook Monument Park.
Chaplin
This attractive small town, named after the early landowner and surveyor Deacon Benjamin Chaplin, is a part of Windham County in the Northeastern Connecticut Planning Region. Chaplin’s natural splendor and rural charm make it an apt locale for outdoor recreation. Vacationers can fish in the nearby waterbodies, kayak along the Natchaug River, explore the hiking and equestrian trails in the Natchaug State Forest and Diana’s Pool, or take a tour of the Chaplin Museum, the Witter House, and the Chaplin Historic District, that covers the town’s historic village center extending for 0.8 miles along Chaplin Street.
Washington
Washington, a cute rural town in Northwestern Connecticut’s Litchfield County, is celebrated for its historic architecture, vibrant culture, and magnificent natural surroundings featuring the Shepaug River, Lake Waramaug, Mount Tom State Park, and Meeker Swamp. Home to a population of 3,646 inhabitants as per the latest US Census, the rolling hills, high plateaus, river valleys, expansive farmlands, peaceful country roads, and carefully preserved historic homes give Washington a quintessential New England atmosphere. In addition, the town is home to several family-owned stores, specialty retail shops, art galleries, museums, and fantastic restaurants. The various community events, like the Harvest Festival and Holiday in the Depot, also draw thousands of merrymakers to Washington every year.
Litchfield
The former administrative center of Litchfield County, Litchfield, is located in the state’s Northwest Hills Planning Region, approximately 95 miles from New York City’s Central Park. The splendid natural scenery and plenty of beautifully restored colonial-era buildings at the village center captivate everyone who visits this classic New England town. To learn more about the town’s rich past, history buffs must not miss the Litchfield County Jail, Litchfield History Museum, Tapping Reeve House & Law School, and the White Memorial Conservation Center. Nature enthusiasts are free to explore the several miles of trails in Topsmead State Forest that provide breathtaking views of the adjacent landscape.
Cornwall
Set at the foothills of the Berkshire Mountains in Litchfield County, Cornwall is esteemed as the “Home of the Covered Bridges” that has been spanning the Housatonic River since 1864. However, only one of these bridges has survived the test of time and is currently a well-known tourist destination and among the state’s most-photographed locations. Moreover, the town’s landscape comprises an expansive portion of forested land, which includes several acres of Mohawk State Forest, resulting in Cornwall often being christened the “Greenest Town in Connecticut.” Besides the West Cornwall Covered Bridge, some of Cornwall’s interesting sites include the 42-acre Cathedral Pines nature preserve, Cornwall Bridge, Cornwall Bridge Station, Cornwall Library, and Mohawk Mountain Ski Area. The town’s proximity to other significant metropolitan areas has made it an attractive destination for tourists and residents alike.
Essex
Essex, a small town known for its outstanding scenery and interesting architecture, is located along the Connecticut River shores in Middlesex County and forms a part of the Lower Connecticut River Valley Planning Region. A quick stroll through the town’s Main Street, filled with numerous small shops, boutiques, and restaurants, reveals why Essex is considered the “Best Small Town in America.” The town’s well-maintained colonial-style structures and enticing village center will fascinate the tourists. Some other noteworthy attractions include the Connecticut River Museum, the Essex Steam Train, the iconic Ivoryton Playhouse (Comstock-Cheney Hall), Benjamin Bushnell Farm, Centerbrook Congregational Church, Pratt House, Essex Art Association Gallery, Griswold Inn, and the Copper Beech Inn. Essex also hosts various annual celebrations, including the Connecticut River Eagle Festival, a Groundhog Day parade, a Loser’s Day parade, and a “Shad Bake” sponsored by the Rotary Club of Essex on the first Saturday of June every year.
Kent
A gateway to the idyllic Northwest Corner of Connecticut, this quaint New England town is located approximately 90 miles north of New York City. History and modernity coexist peacefully in Kent alongside magnificent scenic beauty, making it an ideal refuge for nature lovers. Travelers visiting Kent must explore the many interesting sites, including the Kent Barns complex, the 2300-acre Macedonia Brook State Park, the Kent Falls State Park offering views of amazing waterfalls, the Bull’s Bridge across the Housatonic River, the Sloane-Stanley Museum housing antique collections of American painter Eric Sloane, and the Connecticut Antique Machinery Association museum that restores antique machinery and educates the visitors about the industrial and agricultural history of the state. Every year, the town hosts many annual events, such as the Sidewalk Festival, the Christmas Tree Lighting Ceremony, the Parade of Lights, and a series of outdoor summer concerts by local bands on the lawns of the Town Hall.
Madison
An alluring small coastal town, Madison is located in the southeastern corner of New Haven County, at the heart of the state’s Long Island Sound shoreline. The town welcomes visitors to enjoy its waterfront serenity with its spotless sandy beaches, pleasant downtown, and friendly locals. Vacationers can spend a relaxing time at the Hammonasset Beach State Park or take a leisurely stroll through the downtown, browsing its many bookstores, coffee shops, cafes, gift boutiques, restaurants, and the iconic E.C. Scranton Memorial Library. History buffs can explore the town’s many fascinating sites, including the Allis-Bushnell House, Hammonasset Paper Mill Site, Meigs-Bishop House, Jonathan Murray House, and the Madison Green Historic District.
Monroe
Primarily considered a bedroom community of Bridgeport, New Haven, and New York City, this small town in Fairfield County forms a part of Connecticut’s Greater Bridgeport Planning Region. Named in honor of US President James Monroe, the town is well-known for its rich history besides its spectacular natural beauty. Some of Monroe’s famous attractions that tourists must visit include the Warrens’ Occult Museum, Stepney Cemetery, Monroe Center Historic District, Daniel Basset House, Monroe Green, and the Stevenson Dam Hydroelectric Plant. Nature lovers are drawn to Monroe’s abundant natural sites like the Webb Mountain State Park, the William E. Wolfe Park at the southwestern corner of which is the Great Hollow Lake, and the Housatonic Railway Trail - a five-mile section of the picturesque Pequonnock River Trail.
Putnam
Initially referred to as Aspinock, this enchanting town on the banks of the Quinebaug River in Windham County forms a part of the Northeastern Connecticut Planning Region. Tourists visiting Putnam can walk down the town’s refurbished “Historic Downtown” and browse its wide array of antique stores, exquisite boutiques, theaters, art galleries, cafes, and restaurants. To learn more about Putnam’s glorious past, make sure to visit the Gertrude Chandler Warner Boxcar Children's Museum and the Putnam County Historical Society & Museum. In addition to indulging in various delicious cuisines served by the town’s famed restaurants, tourists can also participate in a variety of recreational activities, such as hiking the 2-mile-long Putnam River Trail, which follows the eastern shore of the Quinebaug River, which provides awe-inspiring views of the Cargill Falls.
Westport
Placed along the shores of the Long Island Sound at the mouth of the Saugatuck River within the state’s Gold Coast, this attractive seaside town is a part of the Western Connecticut Planning Region, approximately 52 miles northeast of New York City. With its spotless sandy beaches such as Compo Beach and Burying Hill Beach, spectacular riverfront parks like the Sherwood Island State Park, alluring marinas, art galleries, performing arts venues, and a cluster of small businesses and eateries, Westport is the most sought-after destination for residents and visitors alike. Tourists visiting Westport can also tour other noteworthy attractions like the Westport Country Playhouse, Westport Museum of Contemporary Art, Westport Museum for History & Culture, the Rolnick Observatory, Earthplace Natural History Museum, and the Wakeman Town Farm.
Colebrook
Home to a population of only 1,361 inhabitants, Colebrook is beautifully nestled amidst rolling hills and luxuriant greenery in Litchfield County, which forms a part of the Northwest Hills Planning Region. Named after the village of Colebrook in Devon, England, this unspoiled New England town delights visitors with its vivid colors during the fall season. Vacationers can enjoy recreational activities like hiking and wildlife viewing at the Algonquin State Forest, besides amazing panoramic views offered by the Gaylord Pond Dam and the Colebrook River Lake Dam. The Norbrook Farm Brewery serving craft beers is the perfect place in Colebrook to hang out with your friends.
From its coastline along the Long Island Sound to the Litchfield Hills, the nation’s third-smallest state by area and the 29th most populous state is full of beautiful small towns. Each of these towns showcases the state’s eye-catching natural landscapes, historic sites, thriving cultures, and a plethora of recreational activities. Widely known for their splendid sceneries, friendly locals, and peaceful atmosphere, do not miss traveling to these small towns on your next vacation to the Constitution State.
