8 Towns in Connecticut That Have the Best Main Streets
Though the state of Connecticut is small in size, spanning only 5,018 square miles, it is mighty in main street energy. The state, nestled in the northwest, near New York and Rhode Island, boasts arts and culture, exquisite cuisine, and stunning waterside views, such as Connecticut River's North Cove and South Cove. While some towns overpour with historical lodgings, others have sandy beaches and expansive boardwalks. Whichever of these towns in Connecticut you choose, you are sure to find exquisite natural wonders, rich histories, and loads of maritime culture, all packed into the main streets.
Ridgefield
Small lakes dot this small town, including Mamanasco Lake, Lake Naraneka, and Fox Hill Lake. Fox Hill Lake sits beside Bennetts Pond State Park. To the west, explore Limestone Preserve Trailhead. It starts at an old railroad and continues into a collection of wood paths and paved footpaths. Back in the town’s main streets, stop by Aldrich Contemporary Art Museum and admire exhibits of contemporary art. Some exhibits are really out of the box, such as a giant baby and one made out of grocery bags. In the town’s core on Main Street, explore a plethora of stores. Interiors & Designs by Ursula offers handmade jewelry and boutique interior design services. Books on the Common is an independent bookstore that sells old and debut novels. Chat with the staff to get your next reading recommendation. Hungry after exploring? Check out The Lantern, with its leader being a master Italian Chef.
Middletown
Middletown is a gem of a town nestled along the Connecticut River. Nature enthusiasts enjoy a visit to Wadsworth Falls State Park. It is a great spot for hikers and bikers, and to admire the majestic falls. Unfortunately, swimming and eating around the Big Falls is not allowed, with the falls’ main purposes being nature views and photography. If you are an art lover, then you are in luck, as Middletown’s main streets house the Davison Art Center, which has over 25,000 works. The town’s main streets also boast a delicious and widely known brewery: Stubborn Beauty Brewing. For a decade, the brewery has continued to give residents and tourists samples and full howlers. Try a Happy Treez IPA or a Belgian Secret Agent.
Essex
The west of this town houses a decent portion of the Connecticut River, with both the North Cove and South Cove, and throughout the town are various other river systems: Falls River, Falls Pond, and Tiffany Brook. This means there are plenty of water views within the town’s main streets. Some town parks to explore include Stanley Park and Fall River Park. For extra river views and to learn about the 1812 war history in the area, visit the Connecticut River Museum. The exhibits and relics inside outline the British Raid that happened in 1814. Additionally, get your fill of boutique shopping at You Me and the Sea and J. Alden Clothiers. You Me and the Sea offers unique gifts you will not find elsewhere, like sea glass jewelry and seaweed pressings, which look stunning as wall art. At J. Alden Clothiers, find the finest clothes for men and women.
Westport
This beautiful small town’s shores sit right on the Long Island Sound, providing water views for miles. Right on the shore is Sherwood State Park. It offers a family-friendly area with a picnic set up with access to swimming in the sound. To soak up all the nature views, walk to the observation area at Sherwood Island and see marsh flora and fauna. The main streets of this town also offer a unique astronomy experience. Head to the Westport Observatory at night to get a closer look at the stars. They use a Celestron EdgeHD telescope, which allows people to see the patterns of the moon and eclipses. A top store to explore is Savvy + Grace, which provides beach and town-inspired merch, like shirts and travel cups. Other stores include Lululemon and Tiffany & Co. To eat, visit Rye Ridge Deli or Manna Toast Cafe.
Darien
Darien, Connecticut, also sits along the Long Island Sound’s edge, but it boasts different activities on its main streets. Its shores have pockets of water, like Goeller Cove and Ziegler’s Cove. A couple of parks to explore in the town include Woodland Park and Cherry Lawn Park. A hot commodity in this town’s core is Pear Tree Point Beach. Along the sandy beach are wooden lawn chairs, which people use for free. Open to the public and safe for swimming, the beach also contains grills and a gazebo. For an indoor marine experience, visit Maritime Aquarium at Norwalk, boasting 75 live exhibits and highlighting 300 different species of marine animals. Next, grab a pint at Lock City Brewing Company. They offer a collection of tap IPAs, and it is pet-friendly.
Niantic
Niantic, Connecticut’s name comes from the bay it resides on, Niantic Bay. The large curve of shoreline houses the town’s main streets that overflow with parks, lodgings, and marinas. View Wigwam Rock in the bay from McCook Point Park, which also has a beach, or get harbor vibes from Niantic Beach and Niantic Boardwalk. Between these destinations are a plethora of restaurants that all foodies will love: Skippers Seafood, The Black Sheep, Café Sol, and Gumdrops & Lollipops Candy & Ice Cream. Niantic’s small-town streets offer a variety of relaxing and food experiences and have a buzzing atmosphere.
Mystic
Mystic is a small town on the shores of Mystic River and contains several places to stay and eat. It also offers cultural and recreational experiences. For a waterside view, stay at Whaler’s Inn. The inn offers a historical and nautical vibe and has been in the downtown core for 125 years. In total, there are 16 guest rooms in the main inn with queen and king beds, and the famous The Shipwright’s Daughter is a part of the area, offering breakfast and dinner. Another top restaurant is Red 36, which serves seafood, and American cuisine. For an outdoor experience, head to Williams Beach Park. There is a small playground equipment area, and it is a fantastic spot to cool down in the waters. To learn about Mystic’s original waterfront settlement, visit Mystic Seaport Museum.
Chester
Tucked between the Connecticut River and Cedar Lake, Chester is a charming town surrounded by stunning natural scenery. Other water systems in the town are Pattaconk Reservoir and Deep Hollow Reservoir. There are several green areas and parks residing along these waterways, like Gillette Castle State Park and Constance Baker Preserve. Aside from that, walk along the boardwalks at Hays Haven Marina and then stop for a bite to eat at The Anchor or Marker 37. The chefs at Marker 37 produce a seasonal menu and cook meals like salmon piccata and yellowfin tuna. As a bonus, they allow boaters to dock their boats in an attached docking station on their property.
These towns in Connecticut have the best main streets with authentic breweries, state parks, beaches, lakes, and historical sites dotting the curbs. You will also find top-tier seafood restaurants, as well as unique, small-business shops to buy souvenirs and gifts. Despite being the second smallest state by area, Connecticut has a wealth of history and culture on the main streets of its small towns.
