9 Towns in Connecticut with Vibrant Downtown Areas

There’s more to Connecticut than commuter trains and hedge fund mansions; the Nutmeg State also boasts several towns that exemplify the best of small-town culture. From bustling downtowns filled with unique shops and delicious food options to picturesque villages along the Connecticut shoreline, this small state offers big adventures for anyone with a car and some time on their hands. Here are some of our favorite towns in Connecticut whose downtowns will keep you entertained and educated!

Mystic

First on many lists about Connecticut should be its nautical gem, Mystic. Perhaps most famous for the Julia Roberts film “Mystic Pizza,” visitors can visit the same restaurant today and enjoy the film looped 24/7 inside while munching on its distinctive pan pizza. Those more commercially minded can stroll downtown Mystic and stop for ice cream by the drawbridge or even stroll Olde Mistick Village, a ramshackle selection of crafty boutique shops within a few minutes' stroll of the nationally-acclaimed Mystic Aquarium. For history lovers, the Mystic Seaport Museum is a living history museum that features multiple tall ships that can be boarded, live demonstrations, and even periodic sea chantey singing. Its art exhibitions aren’t to be missed! Nearby, there are also several beaches caressed by the Atlantic, and Rhode Island is just a few miles away.

New Canaan

Reachable via road or MetroNorth train, New Canaan sits on the border between New York and Connecticut, making it an easy treat for anyone in NYC. A luxurious downtown, just steps away from the train station, features designer shops like Ralph Lauren, countless restaurants, and architectural gems. A few blocks away is the iconic (and tempting) Glass House, designed by Philip Johnson, which offers tours and gardens to stroll. The New Canaan Historical Society offers tours and exhibitions on the local history as well as a listing of local landmarks in the area, like “Mid-Century Modern New Canaan.”

Ridgefield

Ridgefield is in the foothills of the Berkshire mountains and boasts a tranquil downtown blending historic-colonial charm and more modern sensibilities. Start with the Aldrich Contemporary Art Museum, one of the nation’s oldest contemporary art museums, and enjoy the avant-garde in visual art through one of its many exhibitions. Drama enthusiasts should check out the Ridgefield Playhouse, a venue that offers not just theatrical productions but also films and concerts as well. For those interested in New Canaan’s colonial history, we recommend the Keeler Tavern Museum & History Center, which sits on a tavern site dating back to 1713. This living history museum will show what New Canaanites of the 18th and 19th centuries did daily and provide a lovely historical bookend to the forward-looking Aldrich.

Westport

Another stop on the MetroNorth Railroad, Westport, is near the shoreline in Fairfield country and brings artistic flair to the banks of the Saugatuck River. Theater lovers can look forward to larger productions at the Westport Country Playhouse, a regional theater that has hosted countless dramatic luminaries. Music fans can look forward to free concerts. Those looking to relax can go to Compo Beach, where the gentle waves of the long island sound will simply lap onto shore. Another option for music lovers is the Levitt Pavilion for the Performing Arts, an outdoor venue offering free concerts and events throughout the summer.

Guilford

Guilford is the epitome of quaint coastal Connecticut, and its small but charming downtown boasts a classic New England-style Green that is surrounded by restaurants, cafes, shops, and galleries. The Green itself hosts a farmers’ market, art shows, and community gatherings and thus is its own attraction. Additionally, Guilford’s coastal status boasts a variety of bike trails and the small Jacobs Beach on the Long Island Sound, where you can smell the salt breeze and enjoy a day by the water. For history buffs, the Henry Whitfield State Museum boasts the oldest house in Connecticut, built in 1639, and shows a slice of colonial history. Guildford is very accessible via road or train as it is on the Shoreline East rail line as well as I-95.

Bethel

Bethel is a tiny town near the larger city of Redding in the scenic rolling hills of Western Connecticut. It’s a small but mighty downtown strip that offers several restaurants, as well as Broken Symmetry Brewing’s Gastropub, which offers homegrown beer. Nature lovers will enjoy Overlook Park in the middle of downtown, which lives up to its name: it sports scenic views of the rolling hills as well as the historic Poker Rock, a rock known for early 20th-century gambling meetups. Stroll the streets downtown with a coffee from Molten Java and read a book at the Bethel Public Library.

Kent

Kent, in the Litchfield Hills area of Connecticut, offers the perfect mix of nature and civilization. The Kent Green is a shopping zone in the center of downtown, with boutiques, cafes, and antique stores offering the best of colonial furnishings. Nearby is the Eric Sloane Museum, which is dedicated to the artist/author and showcases his works, as well as a large collection of early American tools and machines. Nature lovers will rejoice in Kent’s proximity to the Appalachian Trail as well as Kent Falls State Park, with some of the state’s loveliest waterfalls.

Old Saybrook

One of the oldest towns in Connecticut (a crowded field), Old Saybrook is a masterpiece of waterfront vistas, historic buildings, and coastal charm. Saybrook Point, on the Connecticut River and Long Island Sound, is a marina and tourist area that provides views and several opportunities for both boating and dining. Those looking to get in the water themselves will enjoy Harvey’s Beach, a small strip of sand with calm waters and beautiful sunset views. Arts lovers will enjoy the Kate, more officially known as the Katharine Hepburn Cultural Arts Center: this multipurpose venue offers live music, theater, film, and more in a historic building that also houses the Katharine Hepburn Museum.

Essex

Not far from Mystic, where we began our journey, Essex lies on the edge of the Connecticut River and sports a small but very historical downtown that embraces nautical and shipping history. Look at the Steam Train and Riverboat that offers scenic rides along the river or the Griswold Inn, a continuously operating inn dating back to the 19th century that features group Sea Shanties singalongs every Monday since the 1970s. The Pratt House museum showcases a well-preserved 18th-century home and sets the scene of Essex’s history, connecting shipping routes with the local inhabitants. Its main street leads down to the water, and on still nights, one can see the lights of Mystic just down the water. It doesn't get better than this if you're looking for a classic coastal New England feel.

Connecticut offers so much more than long commutes or large insurance meccas: its small towns are full of character and history and oftentimes are connected intimately with nature. Each of them is worth a stroll, and most are accessible via train from New York City, Hartford, or New Haven, making them the perfect destinations for a day trip to get out of the city. Whether it’s in the spring blooms or the autumnal charms of New England, these small towns are well worth the trip through the Nutmeg State.