8 Eclectic Small Towns In Connecticut
Connecticut, the southernmost state in the Northeastern US’ New England region, is bounded by the Long Island Sound in the south and the adjacent US States of New York, Massachusetts, and Rhode Island on the west, north, and east, respectively. Placed betwixt two thickly populated urban sprawls, Boston and New York City, the Nutmeg State, with its enticing yellow-sand beaches, forested elevations, and town squares, portrays a mingle of bucolic settings, heritage sites, and modernistic metropolitan lifestyle. Nevertheless, the largely unnoticed eclectic towns spotting Connecticut’s 4,849 sq. mi. terrain are flawless destinations for sojourning on your short-hauls or extended breaks.
Litchfield
Litchfield County’s former administrative capital, labeled after its namesake cathedral city in England’s Staffordshire, is situated around 95 miles from New York City’s Central Park in the Northwest Hills Planning Region of Connecticut. The eye-catching natural spectacle and loads of scrupulously restored heritage properties fascinate everyone who visits this classic New England gem. To gain knowledge about the town’s bygone years, history connoisseurs should survey the Litchfield County Jail, White Memorial Conservation Center, Litchfield History Museum, and Tapping Reeve House & Law School, while trekking miles of trails in the 615-acre Topsmead State Forest provide nature fans with jaw-dropping vistas of the conterminous landscape.
Chaplin
Named for the pioneer settler Deacon Benjamin Chaplin, this appealing Windham County town is a part of the Northeastern Connecticut Planning Region. Chaplin’s untouched beauty and backwoods chic make it best suited for outdoor recreation. Excursionists can kayak along the Natchaug River and Diana’s Pool, go fishing in the abutting aqueous bodies, traverse Natchaug State Forest’s equestrian trails, pay a visit to Chaplin Museum as well as National Register-listed Witter House and 40-acre Chaplin Historic District that covers Chaplin’s historic village center extending for 0.8 miles down Chaplin Street.
Washington
An idyllic town in Litchfield County occupying Northwestern Connecticut’s Litchfield Hills region, Washington sits roughly 40 miles west of Hartford and 80 miles northeast of New York City. This 3,646-inhabitant town’s time-honored architecture, energetic civic life, spirited culture, pictographic countryside featuring undulating hills, high flatlands, riverine valleys, wide-ranging cultivated lands, Lake Waramaug, and meticulously preserved medieval buildings give Washington a quintessential New England vibe. Conjointly, peruse the multiple boutiques like Five Janes, art galleries like The Hen’s Nest Gallery, and restaurants like The Po Café, aside from partaking in yearly festivities like Holiday in the Depot and Harvest Festival.
Kent
Located immediately beside the state boundary with New York, this Litchfield County town forms a part of the Northwest Hills Planning Region. A best-loved retreat for globetrotters of all ages, Kent boasts sublime scenic beauty. Sightseers on a tour of Kent must take note of the astounding waterfalls at the Kent Falls State Park, the Kent Barns complex, the Bull’s Bridge across the Housatonic River, the restored vintage machinery preserved at the Connecticut Antique Machinery Association Museum, the 2,300-acre Macedonia Brook State Park, and artist Eric Sloane’s collections at the Sloane-Stanley Museum. Annually, try to be present at the Christmas Tree Lighting Ceremony, Parade of Lights, Sidewalk Festival, and an open-air summer concert series performed on the Town Hall lawns by local bands.
Chester
Chester, baptized after the county town of Cheshire in North West England, is a teeny rural Middlesex County town in the Lower Connecticut River Valley Planning Region of south-central Connecticut. Originally a shipbuilding community and a New England mill town, Chester wonderfully blends its rich heritage with modern-day amenities. Numerous painstakingly maintained colonial-era properties fill the town’s charming Main Street and house plethoric home goods stores like The Little Shop by Nora Murphy Country House, clothing stores like Amber and Lowell, art galleries like Chester Gallery, and first-class restaurants like The Village Bistro.
Throughout the year, tourists are enthralled by the town’s notable attractions, including The Old Town Hall, Goodspeed Opera House - Norma Terris Theatre, Chester Museum at the Mill, Villa Bella Vista, Jonathan Warner House, Charles Daniels House, Dr. Ambrose Pratt House, and Beth Shalom Rodfe Zedek synagogue. Outdoor enthusiasts should explore the Chakana Sky Alpacas Farm and the Cockaponset State Forest, as well as enjoy a ride aboard the Chester-Hadlyme Ferry.
Westport
A bewitching coastal town in southwestern Connecticut’s Fairfield County, Westport is located on the state’s Gold Coast alongside the Long Island Sound shores, approx. 48 miles northeast of the Big Apple. Residents and vacationists alike are drawn to this Western Connecticut Planning Region town lured by its ultra-clean sandy beaches such as Compo Beach and Burying Hill Beach, arresting waterfront parks like Sherwood Island State Park, enticing marinas like Ned Dimes Marina, art galleries like Sorelle Gallery Fine Art, live music venues like Levitt Pavilion, clothing stores like Mitchells, and eateries like Nômade.
Likewise, when in town, touristic places such as the Westport Country Playhouse, Rolnick Observatory, Westport Museum for History & Culture, Earthplace Natural History Museum, Wakeman Town Farm, and Westport Museum of Contemporary Art are must-visits.
Old Saybrook
This Middlesex County, set at the conflux of Long Island Sound and Connecticut River, is one of the Nutmeg State’s oldest towns. Old Saybrook ardently contributes to the area's economy and business growth, being the Lower Connecticut River Valley’s commercial, retail, and small manufacturing mecca. The town’s inviting Main Street is chock-a-full of home goods stores like Driftwood of Old Saybrook: Unique Gifts & Home Décor, boutiques like Pearls & Plaid, gift shops like Cottage Flair, and diners like Mirsina’s Restaurant.
Additionally, drop by the noteworthy sites of interest such as John Whittlesey Jr. House, Black Horse Tavern, Connecticut Valley Railroad Roundhouse & Turntable Site, Saybrook Breakwater Lighthouse, and Lynde Point Lighthouse; traverse the hiking trails at Gardiner’s Landing & Fort Saybrook Monument Park, and Great Cedars Conservation Area; and enjoy theatrical performances at Katherine Hepburn Cultural Arts Center.
Cornwall
Christened after the ceremonial county of Cornwall in South West England, this 1,567-inhabitant community sits at the foothills of the Berkshire Mountains in the rustic Litchfield County’s northwestern portion. Formally incorporated in 1740 and forming a portion of the Northwest Hills Planning Region, Cornwall is best known as the “Home of the Covered Bridges” in connection with the West Cornwall Covered Bridge that has since 1864 spanned the Housatonic River in addition to being one of the state’s key tourist spots and most-photographed locations.
Furthermore, the town’s terrain features sweeping woodlands comprising acres of Mohawk State Forest, which has fittingly earned the town its sobriquet the ‘Greenest Town in Connecticut.’ Also, the Cathedral Pines Nature Preserve, Cornwall Bridge Station, Mohawk Mountain Ski Area, and Cornwall Library are some unmissable sites.
From rural gems like Washington and Chaplin to the shoreside town of Westport, the 29th most populous and 3rd smallest state of the nation packs a number of little-known towns within its borders. Each of these charismatic hamlets, with their awesomazing sceneries, engrossing histories, overbounteous leisure-time activities, kaleidoscopic seasonal celebrations, and the warm hospitality of dwellers, has a whole lot to offer for everyone. So, if you are looking for a scenic locale to spend your holiday or are planning to relocate to a tranquil place with dear ones, look no further than these composite towns in the Constitution State.
