7 Best Downtowns In Connecticut
Connecticut, located in the northeastern United States, is a haven for diverse culinary scenes, arts and culture, rich history, and breathtaking views of the Connecticut River. Each town, such as Westport, with its long boardwalks and sandy beaches, or Essex, with its historic landmarks and attractions, and, of course, their charming downtowns, offers a unique experience waiting to be discovered. No matter when you visit, these smaller communities promise a variety of experiences that make their bustling downtowns must-visit destinations in Connecticut.
Essex
Essex, a small town in Middlesex County, is highly regarded for its walkable downtown district, which features a mix of art galleries, shops, and restaurants. The Spectrum Art Gallery and Artisan Store is a wonderful place to start exploring the town’s art scene, as it offers diverse artwork ranging from sculptures to paintings. Each month, classes and workshops are held for those wanting to learn more about different art forms. Local artisans also showcase their handmade jewelry, pottery, glass art, ceramics, and fashion items. Nearby, you’ll find handcrafted candies, truffles, and warm chocolate chip cookies in specialty stores such as Chocolate Geeks and Joy Chocolate Co.
The Connecticut River Museum, housed in a restored 1878 steamboat warehouse, is also on Main Street. The museum features displays and exhibits that highlight the area’s maritime history. Depending on the season, it offers afternoon and sunset cruises with excellent river views. Nearby, Main Street Park is a great place to take a stroll, have a picnic, or enjoy nature. For lodging, the historic Griswold Inn offers charming rooms, a restaurant, a wine bar, a taproom, and art tours, offering a comfortable and enjoyable stay in downtown Essex.
Manchester
Manchester, a short drive from Hartford, Connecticut’s capital, is a delightful blend of big-city convenience and small-town charm. The heart of its downtown district, Main Street, is a food lover’s paradise. It offers diverse eateries, from gourmet burgers and British fare to thin-crust pizza and Jamaican cuisine. The street and its surroundings are also dotted with cozy coffee shops, ice cream parlors, cafés, convenience stores, delis, and markets.
Beyond the culinary delights, downtown Manchester has plenty to offer. The Firestone, an art studio, is a haven for artists looking to unleash their creativity with pottery painting, glass fusing, and wet clay classes. For those keen on delving into Manchester’s history, the Old Manchester Museum is a must-visit.
Main Street comes alive on the second Saturday of every month with local shopping, gallery exhibits, live music, and enticing food and beverage deals. Additionally, the annual Cruisin’ on Main has been a beloved Manchester tradition since 2001, featuring a lively car show, food vendors, and entertainment. As the seasons change, the town buzzes with events such as the Downtown Scarecrow Festival, the Manchester Road Race, and Holiday on Main.
Ridgefield
Ridgefield boasts one of Connecticut’s most vibrant downtowns and is well known for its varied art and cultural environment. The Aldrich Contemporary Art Museum is the perfect place to see modern art in the center of Ridgefield’s historic district. The museum’s sculpture garden is even more fascinating, with landscaped paths, native plants, and an amphitheater. For further sightseeing in the art realm, visit the Ridgefield Guild of Artists. More than just an art gallery, it’s an ideal place to attend a workshop, enroll in a class, or sit in on a lecture.
In terms of entertainment, since 1965, the Ridgefield Theater Barn has presented comedies, dramas, and musicals for the neighborhood. The theater offers workshops and classes in addition to its many performances. The Ridgefield Playhouse, another prestigious performing arts theater, is located nearby. The Keeler Tavern Museum & History Center is open seasonally and must-visit for anybody interested in being transported back to Ridgefield's early days.
New Canaan
Nestled in the southwest of Connecticut, the quaint town of New Canaan offers a small-town vibe and a lot of personality. Explore the town's culinary scene by visiting Spiga on Main Street, which serves pizza, pasta, and charcuterie boards. Elm, a well-liked local restaurant with afternoon tea service on Fridays and a delicious brunch on Saturdays and Sundays, is located a few blocks down. Another well-liked eating spot is Blackbird, a chic setting for small plates and wine.
Nearby, take an art class at Silvermine Arts Center, stroll the trails and gardens at the New Canaan Nature Center, or visit notable local sites like Grace Farms and the Glass House. Downtown New Canaan is usually bustling with activity, regardless of the season. Food festivals, art fairs, and sidewalk sales occur in the summer, while Christmas celebrations fill the streets during the winter.
Chester
Chester boasts one of the nicest downtowns in the state and is tucked away in the scenic Connecticut River Valley. Grano Arso, an Italian restaurant in the area, is considered one of Connecticut's best dining options. Another well-liked restaurant is River Tavern, which serves lunch, dinner, happy hour, and brunch. Chester's downtown also offers a plethora of enjoyable activities. Visit the Chester Museum at the Mill to learn about local history, see a musical performance at the Terris Theatre, and stroll around the Lori Warner Gallery, which also serves as a boutique.
Take the Chester-Hadlyme Ferry from downtown to Gillette Castle State Park, one of the town's main attractions. The park's most notable feature is the contemporary medieval stone castle constructed by William Hooker Gillette, best known for his depiction of Sherlock Holmes.
Westport
Westport, a quaint town with a busy downtown full of attractions, is situated along the Long Island Sound on the Gold Coast. Explore the upscale boutiques and small businesses along Main Street before heading to eateries like Casa Me or Joe's Pizza & Italian Restaurant. Add entertainment to your list of things to do after dining and shopping. From classic comedy to plays, Westport Country Playhouse has plenty to offer everyone. The Levitt Pavilion, a famous amphitheater on the Saugatuck River's banks, is one of the best outdoor locations to see a live performance.
The Westport Public Library, located downtown, provides programming for children, teens, and adults, such as storytime events, film workshops, classes, lectures, and concerts. It also has art galleries, a gift store, a recording studio, and a café with picturesque views. The Museum of Contemporary Art, Connecticut, is nearby and has many exhibitions, education programs, and performing arts events. Westport is also well-known for its stunning beaches, which are the ideal places to unwind after touring downtown.
Mystic
Mystic, one of New England’s most popular tourist destinations, is a seaside town tucked away on the banks of the Mystic River. Its downtown area has stores on Main Street, like Burgee Mystic, which sells home products and apparel for the beach, and Queenie's Gift Emporium, where you can shop for unique items for yourself or your loved ones. Regarding nearby restaurants, Mystic Pizza, a nostalgic pizzeria influenced by the 1988 movie of the same name, offers pies in a space packed with memorabilia. With a tagline like "A Slice of Heaven," it's a place you should try while in town. Stroll from Main Street to Water Street to the Mystic River Chocolate Cafe for specialty chocolates, coffee beverages, or housemade craft beers.
For things to do in the area, the Mystic Museum of Art has fascinating exhibits and events where you can learn more about the artwork featured there. The Mystic Seaport Museum, the top maritime museum in the country, is another excellent museum in the downtown area. Aside from its exhibits, it offers shipyard tours, sailing lessons, engaging lectures, and on-site dining and retail opportunities. Visit Olde Mistick Village, an outdoor space with stores, boutiques, and restaurants that evoke a New England village from the 18th century after leaving the museum.
Discover Connecticut’s Best Downtown Areas
Whether you love the great outdoors, are a history buff, or are an art enthusiast, these Connecticut towns offer it all in the heart of their downtown districts. Explore communities such as Westport for a relaxing beach escape or Ridgefield for its vibrant arts scene. Additionally, in towns such as Essex and Manchester, fantastic restaurants, artisan stores, and historic buildings are all within easy walking distance.
