13 Best Small Towns To Visit In Connecticut

Mystic on the coast holds the country's largest maritime museum and the last surviving wooden whaleship. Litchfield in the western hills hosted America's first formal law school in 1784. Putnam in the Quiet Corner turned its old mill buildings into one of New England's biggest antique districts. Greenwich on the Gold Coast hides multimillion-dollar estates behind tree-lined lanes. Each of these 13 small Connecticut towns delivers something specific: a maritime museum, a covered bridge, a country law school, an antique mall, a nature preserve.

Mystic

Mystic sits along the Mystic River where it meets Long Island Sound. The Mystic Seaport Museum is one of the largest maritime museums in the country. It spreads across 19 acres of restored 19th-century buildings and keeps the wooden whaleship Charles W. Morgan docked on site. The Morgan is the last surviving wooden whaling ship in the world. Bridge Street and West Main Street hold independent shops and seafood restaurants. The 1988 film Mystic Pizza put the town on the map for one specific reason and yes the pizzeria is still open. Boat tours leave from the marina for the Mystic River and Fishers Island Sound.

Essex

Essex sits along the Connecticut River about six miles upstream from Long Island Sound. The Connecticut River Museum at Steamboat Dock covers 400 years of river history and includes a working full-scale replica of the Turtle, the world's first combat submarine designed by David Bushnell during the Revolutionary War. The Essex Steam Train and Riverboat runs vintage 1920s coaches up the valley to Deep River, where you can transfer to a riverboat for the return leg. The Griswold Inn opened in 1776 and claims status as one of the oldest continuously operating inns in the country. Dinner is served in dining rooms hung with maritime art. The Ivoryton Playhouse a few miles inland has staged shows since the 1930s.

Cornwall

Cornwall in Litchfield County is best known for the West Cornwall Covered Bridge, an 1864 wooden span over the Housatonic River that still carries car traffic. The Housatonic itself is one of the top trout-fishing rivers in the Northeast and has a designated Trout Management Area running through Cornwall. Mohawk Mountain Ski Area on the edge of town is the smallest of Connecticut's ski hills but holds a quiet distinction: it's where modern snowmaking was first tested in 1949 (the patent followed in 1950). Mohawk State Forest covers more than 3,000 acres for hiking and cross-country skiing.

Chester

Chester is one of three small towns clustered along this stretch of the lower Connecticut River alongside Deep River and Essex. The walkable village center holds galleries, a long-running independent bookstore (Lark), and small restaurants like the well-regarded River Tavern. The Chester-Hadlyme Ferry has been running since 1769 and takes cars across the Connecticut River to Gillette Castle State Park. The cliff-top stone home was built between 1914 and 1919 by actor William Gillette, the original stage Sherlock Holmes. The ferry runs from April through November.

Kent

Kent in the Litchfield Hills is best known for Kent Falls State Park, where the falls drop a total of about 250 feet over a series of cascades visible from a quarter-mile uphill trail. Macedonia Brook State Park a few miles west has steeper terrain and 13 miles of hiking trails including a section of the Appalachian Trail with views into New York's Hudson Valley. The Kent Historical Society runs Seven Hearths Museum in a 1751 colonial house. Downtown Kent has galleries and a few cafes that fill up during fall foliage weekends.

Old Saybrook

Old Saybrook sits at the mouth of the Connecticut River where it meets Long Island Sound. The Lynde Point Lighthouse (1838) and the Saybrook Breakwater Lighthouse (1886) both mark the channel. Main Street holds shops, galleries, and seafood restaurants. The Katharine Hepburn Cultural Arts Center occupies a restored 1911 building once used as town hall and hosts theater, music, and film year-round. The actress lived in Old Saybrook for most of her life and is buried in town. Saybrook Point Park has a boardwalk along the river with views back across to Long Island Sound.

Westport

Westport on Connecticut's Gold Coast has long been a favorite of writers, artists, and Wall Street commuters. The Westport Country Playhouse, founded in 1931, has staged American premieres of plays by Arthur Miller and Tennessee Williams. Paul Newman and Joanne Woodward served on its board for decades. Main Street and Post Road East hold a mix of national chains and independent shops. Compo Beach has 29 acres of public shoreline along Long Island Sound plus a popular skate park. Sherwood Island State Park is the oldest state park in Connecticut, with more beach, picnic areas, and a 9/11 memorial dedicated to Connecticut victims.

Litchfield

Litchfield was settled in 1719 and is one of the best-preserved colonial towns in New England. The town green is ringed by Federal-era homes, a 1789 Congregational church, and the Litchfield History Museum. Tapping Reeve House and Law School (now a museum) was the first formal law school in the United States, founded in 1784. Graduates included two future U.S. vice presidents (Aaron Burr and John C. Calhoun) and three Supreme Court justices. White Memorial Foundation and Conservation Center is a 4,000-acre nature preserve on the edge of town with 35 miles of trails through woods and wetlands. Topsmead State Forest, the former summer estate of Edith Morton Chase, adds more than 500 acres of meadows and woods plus a Tudor-style mansion open for free tours in season.

Madison

Madison sits along Long Island Sound east of New Haven. Hammonasset Beach State Park covers more than two miles of shoreline (the longest of any state park in Connecticut) along with a campground, a nature center, and the historic Meigs Point. Downtown Madison centers on Boston Post Road (Route 1) and includes R.J. Julia Booksellers, a regionally famous independent bookstore that hosts authors year-round. Bauer Park, a working farm in town, hosts seasonal events including a popular Saturday-morning farmers market in summer. Lenny & Joe's Fish Tale up the road on Route 1 is the local seafood institution.

Niantic

Niantic is a borough of East Lyme along Long Island Sound. Main Street holds the Book Barn, a sprawling used bookstore complex spread across multiple buildings and outdoor sheds. The shop carries more than 500,000 books and a notoriously friendly cat population. The 1.1-mile Niantic Bay Boardwalk runs along the water with views to the Sound. McCook Point Park has a small swimming beach. Rocky Neck State Park just east of town has a sandy beach, salt marshes, and a 1930s pavilion built by the Civilian Conservation Corps.

Greenwich

Greenwich is the southernmost town in Connecticut and the wealthiest by household income. Greenwich Avenue is the main shopping strip with high-end retail, restaurants, and galleries. The Bruce Museum near the harbor holds rotating art and natural history exhibitions and recently completed a major expansion. The Audubon Center in Greenwich was the first nature center in the National Audubon Society system and covers 285 acres of woods and meadows with seven miles of trails. Greenwich Point Park (locally called Tod's Point) covers 147 acres of beach and picnic grounds plus a 1909 stone clubhouse used for events.

Putnam

Putnam in Connecticut's Quiet Corner has reinvented itself from a 19th-century mill town into one of the largest antique districts in New England. Main Street is anchored by Antiques Marketplace, a four-story building with hundreds of dealers under one roof. The Gertrude Chandler Warner Boxcar Children Museum sits inside a restored 1920s boxcar near the river and honors the local author who wrote the Boxcar Children series starting in 1924. Restaurants downtown include the popular 85 Main and Mrs. Bridges Pantry. Putnam is also the staging point for the annual First Friday street festivals from May through October.

Chaplin

Chaplin is one of the smallest towns in eastern Connecticut with a population under 2,300. Natchaug State Forest covers more than 13,000 acres in and around town with hiking trails, the Diana's Pool natural swimming hole on the Natchaug River, and access to fly fishing on a designated Trout Management Area. The historic Chaplin village center is on the National Register of Historic Places, with about 60 preserved structures along the green dating from the early 1800s. Local life centers on the Chaplin Historical Society, the Chaplin Public Library, and a few country stores.

Connecticut's Small-Town Pull

The 13 towns above cover most of what makes Connecticut worth a closer look. Each has a defining feature: the working harbor at Mystic, the antique district at Putnam, the colonial green at Litchfield, the maritime museum at Essex, the law school at Litchfield. Connect a few of them on a long weekend and the state opens up.