8 Small Towns in Connecticut With The Best Downtowns
Anything can happen in Connecticut’s small towns. In Mystic, you might find yourself gazing in awe at the Mystic River Bascule Bridge, an architectural marvel across the Mystic River. In Madison, stunning beaches are within easy reach of the downtown area, where you can relax after exploring the downtown's many historical landmarks. Niantic is a book lover's paradise, with the Book Barn offering access to thousands of books for every type of reader. Whatever your idea of the perfect day out or weekend break, these quintessential New England towns deliver.
Mystic
One of Connecticut’s prettiest towns, Mystic is a historic port on the Mystic River whose downtown overlooks a bustling harbor. Before you hit the shops in the area, hit the water. The Mystic Seaport Express is a river shuttle service that departs from downtown and takes visitors along the river to the Mystic Seaport Museum, where you can wander through a replica 19th century seaport village, watch shipbuilders at work in the first shipyard built specifically for preservation in the United States, and tour exhibitions on shipwrecks, whaling, and more.
Take the return ferry trip to head back downtown. Mystic’s Main Street runs across the river via the pretty Mystic River Bascule Bridge, built in 1922, which separates downtown into east and west. You’ll find plenty of places to go souvenir-shopping on both sides, but for something truly unique, head to Danforth Pewter on West Main Street, which sells handmade pewter pieces like ornaments, jewelry, kitchenware, and home goods that are crafted by New England artists. Head back over the bridge to treat yourself to a Mystic tradition. The S&P Oyster Restaurant and Bar has been serving locals and visitors for over 30 years from its beautiful location by the riverfront. Enjoy views of the water while feasting on fresh seafood and seasonal specials.
New Canaan
An inland town, but still considered part of Connecticut’s Gold Coast, New Canaan was first settled in 1715 and incorporated in 1801. Preserving the town’s history since 1889, the New Canaan Museum and Historical Society is the oldest group of its kind in Fairfield County and maintains a small museum just north of Main Street. The Society, housed in the original 1825 Town Hall, hosts historical exhibitions, lectures, events, and walking tours of historic downtown.
New Canaan isn’t just known for its 19th century architecture. There are several more modern homes around town, one of the most striking of which is The Glass House, a property managed by the National Trust for Historic Preservation. Built between 1949 and 1995 by the architect Philip Johnson, the 49-acre property also includes a studio, gallery, pavilion, art sculptures, and landscaped gardens. Tours are available from mid-April to mid-December.
Back downtown, fuel up at a local hotspot that most tourists miss. Cherry Street East has been a staple of New Canaan’s dining scene since 1977 and is a family-run, small-town pub famous for its hearty burgers. If you’re looking for something more upscale, try the Elm Restaurant, which offers a seasonal menu, cool climate wines, and classic cocktails.
Essex
Essex is a charming waterfront town on the Connecticut River with a rich maritime history and a walkable downtown that was featured on the TODAY Show’s “Merriest Main Streets” series.
Take a wander down to the water to visit the Connecticut River Museum, located at Steamboat Dock. The museum offers a virtual “art walk” featuring breathtaking scenes along the Connecticut River’s journey from northern New Hampshire to the Long Island Sound. You can also experience the river firsthand with a trip onboard the Onrust, a replica 1614 vessel, or a nature cruise on the RiverQuest, which offers educational eco-tours. Boat tours run seasonally from spring to fall.
Head away from the water and west on Main Street to make a pitstop at the Essex Coffee & Tea Company, a charming white clapboard cafe that offers gourmet coffee, freshly-baked snacks, and delicious desserts. The cafe also features a small gallery so you can admire the work of local artists while you sip. See more art at Pencil & Wool, a mother-and-daughter-owned art store on Main Street that sells handmade gifts, local artwork, art supplies, and workshops for those looking to learn a new crafty skill.
Madison
A hidden gem on Connecticut’s southern coast, Madison is a welcoming beach town with year-round attractions and a classic New England town green that anchors the Madison Green Historic District. The district contains several notable landmarks, including the Allis-Bushnell House, built in the late 18th century for two families and now maintained by the Madison Historical Society as a museum showcasing the furnishings and architecture of the Revolutionary, Civil War, and Colonial Revival eras. The house is open for self-guided tours on the first and third Saturdays of the month.
Heading along Madison’s central thoroughfare, Boston Post Road, you’ll find the town’s most famous bookstore. RJ Julia Booksellers is an independent bookstore that’s served the town for over 30 years and has won several awards over the years. The store hosts 300 events a year, offers a wide selection of new and backlist titles, and has knowledgeable staff who can help you find the perfect read.
To hit the beach after sightseeing, head south of downtown. With three public beaches and the Hammonasset Beach State Park within easy distance, there’s plenty of choice for those wanting to swim, hike, or simply feel the sand between their toes. The perfect finisher to a day at the beach is an ice cream cone. Browse Ashley’s Ice Cream's mouthwatering selection to find your favorite.
Westport
Westport has a surprising claim to fame. Tucked along the banks of the Saugatuck River where it meets Long Island Sound, the town offers extensive river and coastal access.
Visit the Library Riverwalk and Garden to enjoy beautiful views over the river and take a wander along the accessible walkway. Benches and picnic tables offer options for resting, packing a lunch, or just savoring the riverfront views. Nearby is the Levitt Pavilion for the Performing Arts, home to one of the longest-running outdoor performing arts series in the country. Established in 1973, this unique amphitheater hosts music, dance, comedy, theater performances, and more. The season runs from April to October.
If you’re looking for a bite to eat in downtown Westport, check out the Spotted Horse Tavern. Housed in the historic Sherwood House, built circa 1808, this family-friendly bistro prides itself on serving up fresh, local seasonal ingredients in casual, pub grub classics.
Wethersfield
Also known as Connecticut’s “most ancient town”, Wethersfield is like something out of a storybook, a classic New England village with over 300 years of history in its streets. The town has a very pedestrian-friendly downtown, at the core of which is its historic district, Old Wethersfield. The largest historic district in the state, this area features 50 houses built before the Revolutionary War; 100 built by the time of the Civil War; and another 150 built shortly thereafter.
You can see this history on display in the three houses of the Webb Deane Stevens Museum. The Joseph Webb House and Silas Deane House both hosted George Washington when he made his headquarters in town in the late 1700s. The museum and gift shop are open from May to October. The museum grounds are beautiful but another lovely place for a wander is the Broad Street Green. The town’s historic village green, where livestock used to graze, is now a shady park dotted with ancient trees, including an 1836 copper beech.
In addition to historic homes, Old Wethersfield’s Main Street has a small collection of boutiques and shops. These include the Old Wethersfield Country Store, which sells a little bit of everything. Browse for old-fashioned candies, sodas, kitchenware, home decor, candles, soaps, and vintage toys.
Niantic
A waterfront community on the shores of Niantic Bay and overlooking the Long Island Sound, Niantic has a relaxed seaside vibe and a thriving Main Street that underwent a significant revitalization program in 2010. Main Street runs parallel to the water, providing easy access to Niantic Bay Boardwalk, a 1.1-mile pathway that stretches along the coast between Cini Park and Hole-in-the-Wall Beach.
If you’re visiting with the family, you won’t want to miss the Niantic Children’s Museum, an interactive, hands-on educational experience. Exhibits include the Discovery Room, the Imagination Room, and a fun Outdoor Playscape. The museum is open year-round and suitable for little ones aged between 9 months and 9 years. For more educational fun for the whole family, go shopping at a Niantic icon, the Book Barn. A local landmark since 1988, the store contains over 350,000 rare and gently used books. It also has scenic gardens full of beautiful nooks for reading, and friendly farm animals who are always eager for a meet-and-greet.
New Milford
On the banks of the Housatonic River lies New Milford, a picture-perfect New England town that’s said to be the inspiration for the fictional town of Stars Hollow in the TV show Gilmore Girls.
Fans of the show will certainly recognize the iconic bandstand in the town green, part of the Center Historic District. Surrounding the green are streets filled with beautiful examples of period architecture from Colonial and Greek Revival mansions to Georgian and Victorian homes. Learn more, visit New Milford Historical Society & Museum, which features permanent and temporary exhibits, including an exhibit on New Milford resident Roger Sherman, the only founding father to sign all four documents related to the birth of the nation.
Near the town green, you’ll find Honeybee Books & Tea, a quaint bookstore that doubles as a cafe serving organic snacks, freshly brewed tea, and coffee. You can also pick up the perfect gift thanks to its curated collection of artisanal merchandise and kitchen gadgets. A few doors down is The Hunt, an antiques shop filled with vintage treasures and one-of-a-kind finds.
History and Heritage in Small Town Connecticut
From port towns and coastal resorts to rural villages and sleepy hamlets, Connecticut’s small communities all have their own distinctive character and charm. One of the original thirteen colonies and the birthplace of the Constitution, Connecticut has a rich heritage that’s evident in its small town streets and greens. Whether you’re planning a New England road trip, a romantic weekend away, or a family break, the above list should give you some ideas for outdoor activities, historic sights, dining, shopping, and unique attractions. It’s easy to spend a day exploring these walkable downtowns and still find yourself planning a return visit.
