Connecticut's Best Small Towns For A Weekend Escape
The southernmost state in the American Northeast’s New England region, Connecticut, is bordered by the Long Island Sound and the neighboring US states of Rhode Island, New York, and Massachusetts. Set between two populous metropolises, New York City and Boston, the nation’s 3rd smallest and 4th most densely populated state has much to offer. With its many attractive sandy beaches, marinas, verdant hills, crystal clear water bodies, and village greens abutted by numerous 17th and 18th-century houses, The Constitution State represents an exemplary fusion of heritage sites, pastoral landscapes, and modern-day life. Scattered all over the state’s 4,849 sq. mi. terrain are innumerable small towns that captivate millions of vacationers looking forward to authentic, memorable experiences during their short weekend trips to the Nutmeg State.
Madison
Madison, christened after US President James Madison, is an enchanting coastal community in the southeastern corner of south-central Connecticut’s New Haven County, at the core of the Long Island Sound shoreline of the state. Being a portion of the “South Central Connecticut Planning Region,” this 17,691-inhabitant town welcomes holidaymakers to appreciate its waterfront tranquility together with its ultra-clean sandy beaches, inviting downtown, and affectionate locals. Unwind at the Hammonasset Beach State Park or stroll through the downtown and have a look at the esteemed E. C. Scranton Memorial Library besides the uncountable boutiques, bookstores, coffee shops, cafes, award-winning seafood restaurants like Lenny & Joe’s Fish Tale, and accommodations like The Homestead Bed & Breakfast, Curio Collection by Hilton. Furthermore, interesting attractions such as the Madison Green Historic District, Allis-Bushnell House, Jonathan Murray House, Hammonasset Paper Mill Site, and Meigs-Bishop House should not be missed.
Kent
This quirky Litchfield County community is located adjacent to the state boundary with New York, about 26 miles north of Danbury. The beautiful blend of history with modernity in Kent makes it a preferred haven for visitors of all ages and interests. Vacationers must discover the many noteworthy sites including the Kent Barns Complex, Kent Falls State Park, the Sloane-Stanley Museum that houses Eric Sloane’s studio and antique collections, the 2,302-acre Macedonia Brook State Park, the Bull’s Bridge spanning the Housatonic River, and the non-profit Connecticut Antique Machinery Association Museum which preserves and renovates old-fashioned machinery as well as enlightens tourists about the state’s agricultural and industrial past. Have a comfortable stay at The Kent Collection|The Victorian, and try to be present at the town’s yearly events such as the Sidewalk Festival, the Parade of Lights, an outdoor summer concert series by local bands on the Town Hall lawns, and the Christmas Tree Lighting Ceremony.
Mystic
Mystic is a vintage resort village and census-designated place located along the shores of Mystic River in New London County’s Groton and Stonington towns. This celebrated holiday retreat comprises three significant historic districts: Mystic Bridge Historic District, Mystic River Historic District, and Rossie Velvet Mill Historic District. Sightseers must tour the Mystic Seaport Museum - one of the world’s leading and the country’s major maritime museums, and observe the classic vessels, research library, over 500 age-old watercraft, maritime art gallery, and a reconstructed 19th-century seafaring village. Also, enjoy a lovely cruise down the Mystic River, or pay a visit to the Mystic Museum of Art and the Mystic Aquarium & Institute for Exploration. Countless gift shops, cafes, bakeries, galleries, seafood restaurants like The Mariner, and boutique hotels like The Whaler’s Inn fill the business district on either side of the Mystic River Bascule Bridge.
Old Saybrook
One of Connecticut’s oldest and most charming towns, Old Saybrook is situated in Middlesex County at the meeting point of the Connecticut River and Long Island Sound. As the retail, small manufacturing, and commercial mecca of the Lower Connecticut River Valley, the town actively contributes to the economic and business growth of the area. Old Saybrook’s flourishing Main Street is packed with a plethora of commercial establishments offering endless shopping opportunities and gourmet experiences. Travelers must inspect the town’s different historically important buildings including Black Horse Tavern, Saybrook Breakwater Lighthouse, Connecticut Valley Railroad Roundhouse & Turntable Site, John Whittlesey Jr. House, and Lynde Point Lighthouse. Supplementarily, watch a theatrical performance at the Katherine Hepburn Cultural Arts Center, recee the hiking trails and traditional walking tracks at the Great Cedars Conservation Area and Gardiner’s Landing & Fort Saybrook Monument Park, and de-stress at Super 8 by Wyndham Old Saybrook.
Essex
Acclaimed for its extraordinary settings and enthralling architecture, this teeny community is located by the banks of the Connecticut River in Middlesex County. The town’s bewitching village center, meticulously preserved colonial-style structures, and the Main Street chock-full of locally-owned shops, boutiques, and restaurants like Noah’s at 63 Main unveil why Essex is thought to be the “The Perfect Small American Town.” The Connecticut River Museum, Ivoryton Playhouse (Comstock-Cheney Hall), Centerbrook Congregational Church, Essex Art Association Gallery, Essex Steam Train, Benjamin Bushnell Farm, and Pratt House are eye-catching points of interest. Have an enjoyable stay at The Griswold Inn and spare time from your hectic schedules to partake in any of Essex’s annual celebrations like the Groundhog Day parade, a ‘Shad Bake’ by Rotary Club of Essex on the first Saturday of June, the Connecticut River Eagle Festival, and a Loser’s Day parade.
Westport
Westport, a lovable seaside community in Fairfield County is located within the state’s Gold Coast adjacent to the Long Island Sound at the Saugatuck River’s mouth. Having marvelous riverfront parks like Sherwood Island State Park, undefiled municipal beaches like Burying Hill Beach and Compo Beach, tempting marinas, performing art venues, galleries, and a bunch of eating joints and small businesses, Westport is a well-appreciated getaway for residents and vacationers alike. When in town, do not forget to explore the Westport Country Playhouse, Westport Museum for History & Culture, Wakeman Town Farm, Westport Museum of Contemporary Art, Earthplace Natural History Museum, and Rolnick Observatory, prior to getting a good night’s sleep at The Inn at Longshore.
Chester
Named after the county town of Cheshire, England, Chester is a tiny rural town in the Lower Connecticut River Valley Planning Region in south-central Connecticut’s Middlesex County. Originally a mill town and shipbuilding community, Chester holds in high esteem its rich heritage in addition to providing modern-day amenities. Carefully maintained landmark properties housing multiple shops, art galleries, boutiques, cozy restaurants like River Tavern serving delectable New American cuisines, and upscale accommodations like The Millhouse Downtown Chester line the town’s meandering Main Street. The Old Town Hall, Chester Museum at the Mill, Charles Daniels House, Beth Shalom Rodfe Zedek synagogue, Jonathan Warner House, Dr. Ambrose Pratt House, Villa Bella Vista, and the iconic Goodspeed Opera House - Norma Terris Theatre draw tourists all year round. Outdoorsy types would love to drop by the Chakana Sky Alpacas Farm, hop aboard the Chester-Hadlyme Ferry, enjoy a refreshing hike at the Cockaponset State Forest, and camp at Camp Hazen YMCA.
Cornwall
Cornwall, called after South West England’s ceremonial county of Cornwall, sits at the base of the Berkshire Mountains in the northwestern part of the rural Litchfield County. Officially incorporated in 1740, the town has also been widely known as the ‘Home of the Covered Bridge’ in reference to the West Cornwall Covered Bridge that has spanned the Housatonic River since 1864 and is one of the most-photographed locations in the state plus a prime tourist spot. Likewise, the town’s topography features wide-ranging forested land comprising several acres of Mohawk State Forest earning the town its moniker the “Greenest Town in Connecticut.” Travelers vacationing in Cornwall must not forget to discover the special sites of interest including the Mohawk Mountain Ski Area, the 42-acre Cathedral Pines nature preserve, Cornwall Library, and Cornwall Bridge Station; and get a homelike feel at the family-friendly Cornwall Inn.
Washington
Home to 3,646 residents as per the latest US Census, this idyllic rural town occupies the Litchfield Hills region in Litchfield County, roughly 40 miles west of Hartford. Washington’s medieval architecture, dynamic civic life, lively culture, and photographic countryside featuring rolling hills, open agricultural fields, high plateaus, Lake Waramaug, and the Shepaug, Bantam, and East Aspetuck River valleys give the town a typical New England ambiance. Additionally, take note of the family-owned stores, art galleries, specialty shops, fantastic eateries like The Po Café, and exquisite country retreats like The Mayflower Inn & Spa, besides finding time to participate in the annual community events such as Holiday in the Depot and the Harvest Festival.
Litchfield
Litchfield, the erstwhile seat of government of northwestern Connecticut’s Litchfield County, forms a part of the Northwest Hills Planning Region approx. 95 miles away from New York City’s Central Park. The spectacular natural landscape and dozens of painstakingly restored colonial-era landmark properties in the village center mesmerize every tourist visiting this quintessential New England community. The Tapping Reeve House & Litchfield Law School, Litchfield County Jail, Litchfield History Museum, White Memorial Conservation Center, and the 947-acre Bantam Lake - the state’s biggest natural lake, are popular sites. Survey the miles of trails in the 615-acre Topsmead State Forest to witness mind-boggling views of the adjoining landscape and rest after an eventful day of explorations at The Litchfield Inn.
Stretching from the northwest Litchfield Hills to the lengthy coastline along Long Island Sound in the south, Connecticut packs plenty of under-the-radar hamlets within a compact area. Each of these gorgeous towns lures tourists worldwide with its awe-inspiring surroundings, gripping histories, colorful annual celebrations, profuse outdoor recreations, homey accommodations, and generous hospitality of the residents. No matter what time of the year it is, these appealing towns are worth adding to your travel diaries if you wish for a fun-filled, refreshing weekend in The Constitution State.
