6 Standout Main Streets In Connecticut

Connecticut is one of the United States' top travel destinations. The state's cultural scene, diverse cuisine, and attractions like Yale University make it a great travel destination. While cities such as New Haven get a lot of tourists, the smaller towns also have a lot to offer. From riverside strolls down streets lined with quaint shops and restaurants to exploring historic attractions, there is something for everyone. The small towns in Connecticut have bustling Main streets with a rich cultural and historical element that make them the perfect spot for meandering and exploring the area. Here we explore six standout Main Streets in Connecticut's small towns.

Essex

Located on the Connecticut River, Essex is a town that looks as if it were straight out of a Christmas card. The Colonial-era buildings lining Main Street and quaint local shops make for a picturesque view. While strolling down Main Street, stop at the historic sites to learn about the town's past before visiting the Connecticut River Museum, located right on Main Street, which features exhibits showcasing the maritime history of the beautiful Connecticut River Valley.

Connecticut River Artisans features handmade items from local artists and is a great spot to find a souvenir to take home. Feeling hungry? Head over to Black Seal Seafood Grille, a popular local spot, for some delicious seafood in a cozy atmosphere. For a coffee, pop into Essex Coffee and Tea Company, or for a dessert, stop by JOY Chocolates for a treat.

Mystic

One of the prettiest towns on the coast of Connecticut, Mystic is one of Connecticut's best towns to enjoy a walk downtown. Lined with shops, restaurants, and beautiful views of the Mystic River, Mystic's Main Street is a lovely spot to visit. Get your photo at the unique Mystic Drawbridge, which connects the two sides of Mystic. A must-visit for history lovers is Mystic's Mystic Seaport Museum, just a few blocks away from the main drag. The museum showcases the town's maritime history and the history of shipbuilding in the area. Throughout the year, seasonal workshops are also held, offering a perfect opportunity for both children and adults to enjoy.

Mystic's Main Street is crawling with shops and restaurants. There are over 80 unique shops and galleries, selling everything from art to clothing and jewelry to food. Trade Winds Gallery Fine Arts is an interesting gallery to visit, featuring original antique maps, charts, and prints. You could also take a cruise with Argia Mystic Cruises, located close to the drawbridge. You can climb aboard virtually anytime of day and enjoy the view of the village from the wooden deck of a sailing ship.

Westport

Westport's Main Street is a hub for culture, shopping, and dining in town. One community attraction just off Main Street is the Westport Country Playhouse. A part of the community since 1931, the playhouse presents a variety of shows, ranging from classic plays to contemporary works. History buffs can enjoy an afternoon at the Westport Museum for History & Culture, located on Westport's Main Street. The Museum was founded in 1889 and today has exhibits that preserve the town's history.

Westport's Main Street is also lined with cute shops and is home to the Westport Farmers' Market, the heart of the community through the fall and summer seasons. This is a great spot to try local produce and support artisans by purchasing handmade products. Some of the more popular stores on Main Street also include Madewell and Faherty Westport.

New Milford

New Milford has a charming downtown with historic buildings and a beautiful Town Green park area. The quaint shops and cafes lining the street create a cozy atmosphere, making it a desirable place to walk around. The Town Green is at the heart of the downtown and is a beautiful green space with a gazebo and lush gardens. This makes it an ideal spot for a romantic afternoon walk or a relaxing family stroll. The Town Green is surrounded by 18th- and 19th-century buildings, such as the Bank Street Theater, which are worth exploring to learn about the town's past. The Bank Street Theater is a historic neighborhood venue with four screens that's been showing major releases since 1902.

The New Milford Historical Society is another excellent spot to visit for anyone seeking to delve deeper into the town's past. There are numerous exhibits and artifacts on display, and it is a great place to learn about the area's history. After walking down New Milford's beautiful Main Street, stop for some Italian cuisine at La Piccolina. A local favorite, this cozy restaurant is a great spot to unwind after a day of exploring.

Chester

Chester is a welcoming town with a vibrant Main Street full of quaint shops and restaurants. On Main Street, stop by The Wayfinder Society for some quirky and unique finds to take home. Afterwards, grab a pint at the next-door Little House Brewing Company or opt to kick your feet back and relax on a ride down the Connecticut River on the Chester-Hadlyme Ferry. The ferry is a unique part of Connecticut's history because it is the second-oldest ferry in the state, having operated continuously since 1769 for over 250 years. The Gillette Castle, easily viewable from the water, is a beautiful historic building that offers scenic views. End the day of exploring with a meal at one of the restaurants on Main Street. Otto is an excellent choice for some pizza, or the Brushmill By The Waterfall offers the opportunity for visitors to enjoy their meal by the water.

Ridgefield

Ridgefield's Main Street is a historic and picturesque place with charming historic architecture, boutique shops, and scenic views. The town dates back to 1709, with Main Street as one of the oldest roads in the area. Main Street is a cultural hub and is a great place to walk around and explore the heart of the community. If you want to delve into the town's past, visit the Keeler Tavern Museum. The beautiful, four-acre site has exhibits on the town's history in the Colonial era through the early 20th century. Nearby, check out some contemporary art at the Aldrich Contemporary Art Museum. The art museum features a 17,000-square-foot facility with two floors of galleries and a sculpture museum located outside. They focus on emerging artists, so prepare to see some unique work! If you need some coffee to fuel your adventures, head over to Corner Café of Ridgefield. The local gem has fresh food for breakfast and lunch as well as local artisanal coffee.

Visiting Connecticut

These six charming Main Streets prove that Connecticut is more than the state of the famous Yale University. Whether you are a history buff, art enthusiast, or shopaholic, there is something for everyone to appreciate about these cute Main Street area. And since these areas and attractions are notably walkable, visitors won't have to worry about driving from one place to the next. Once they are downtown, they can enjoy sightseeing on one street. So next time you are considering a road trip, head to one of these six towns. The vibrant culture of their downtown will make for an experience unlike any other.