9 Off-The-Beaten-Path Towns In Connecticut
The charming vibe of New England on the Atlantic Coast is a truly unmatched experience. Indulge in fresh seafood straight from the source or journey to Connecticut's lesser-known gems. As one of the original 13 colonies, the state is flourishing with historical sites and a long, rich heritage. From the rolling farmlands of Roxbury to cozy Washington in the Berkshire Mountains, there is a piece of paradise in Connecticut, perfect for adventure and relaxing amongst the calming scenery. Discover towns that are a little off-the-beaten-path but well worth the visit.
Essex
Whether traveling by train, boat, or both, the Essex Steam Train and Riverboat are a unique way to get a feel for the area's beauty. Hop onboard the steam locomotive and ride through towns like Deep River and Chester, as well as near nature reserves such as Pratt Cove. Take it up a notch and purchase a ticket for the Dinner Train. Wine and dine for up to two and a half hours onboard a restored vintage locomotive. Feast on a four-course meal featuring seasonal specialties. Continue coasting the area onboard the Adventure Charter and cruise on the Connecticut River. The sunset and fall foliage cruises are not to be missed. Kick back and sail along the waters for up to four hours, taking in the striking Connecticut scenery.
The old-world town of Essex is rich in history and well-preserved colonial masterpieces. Visit the Pratt House, one of Essex's oldest homes and a notable landmark. The residence beautifully showcases vintage heirlooms and antiques, including old kitchen utensils and furniture. From June through September, the museum offers free guided tours on weekends in the afternoon. Get a glimpse of the past at Griswold Inn. Established in 1776, it is one of the longest-running inns in the country. Today, Griswold Inn offers 34 uniquely decorated guestrooms along with a restaurant and wine bar.
Woodbury
Welcome to the Antiques Capital of Connecticut. Woodbury is the place to shop until you drop for quirky finds and vintage treasures. Venture through Woodbury’s Historic District and make a stop at Villa Vintiques on Main Street North. The store proudly showcases and sells a variety of elegant and classic house decor, antique furniture, and locally made art. For vintage items that are a little more cozy, browse the collection at Farmhouse Antiques. Take home a previously loved wooden cabinet, country-style signage, kitchenware, and more.
Woodbury's atmosphere is a seamless blend of natural wonder and a rich heritage. Stunning both inside and out, The Glebe House Museum is a striking example of life in 1740. Browse the museum's collection of 18th-century furnishings. Afterward, take a short walk through the Gertrude Jekyll Garden, which is also on the property. Open year-round, the garden is a tranquil retreat amongst the enchanting flowers. The museum and gardens make for a perfect afternoon or after-breakfast adventure in Woodbury.
Roxbury
Roxbury's expansive wilderness is a selling point. Immerse in Conneticut's dazzling countryside at the Roxbury Land Trust. Explore around 30 miles of trails covering 4,000 acres. Traverse through nature preserves, farmland, and a bewitching mine hill. The non-profit organization is dedicated to maintaining, preserving, and conserving Roxbury's landscape and natural resources. Roxbury Land Trust holds numerous events throughout the year at various locations. Join the locals for Riverfest, mindful walks, owl demos, and turkey talks. The surrounding area is truly one of a kind and showcases the calming landscape of rural Connecticut.
As a farming community, the area naturally has stellar produce and animal products. Toplands Farm is a phenomenal choice, specializing in hormone-free and pasture-raised beef. The farm also houses Double D Living History Farm. Browse the giant collection of antique tractors at Toplands from April to November. Maple Bank Farm is another Roxbury treasure. Visit the property in the summertime for blueberry picking. The farm offers a bevy of produce for sale including squash, potatoes, apples, and leafy greens. It is no secret that farm fresh produce can instantly elevate any dish.
Finish off your personal Roxbury Farm Tour at Riverbank Farm. Take home organic fruits, vegetables, and fresh-cut flowers. Riverbank Farm proudly grows a wide variety of products, including heirloom tomatoes, sugar snap peas, watermelon, sweet potatoes, strawberries, and hot peppers.
Stonington
Steeped in history, Stonington is a captivating and striking coastal Connecticut town. Constructed in 1840, take a tour of The Lighthouse Museum. Climb the staircase at this beautiful stone structure and bask in the panoramic views of Long Island Sound. Inside the lighthouse, browse through a stunning collection of artifacts that showcase Stonington's history, including its maritime roots and items brought back from sailors. Afterward, stroll down Stonington Harbor, the only harbor in Connecticut facing the Atlantic Ocean directly. Frequent visitors to Stonington may wish to purchase a membership at Stonington Harbor Yacht Club and cruise the open waters on canoe, paddleboard, sailboat, or powerboat.
New England's fresh and local cuisine is a top-tier experience. Savor waterfront dining at Breakwater. Imagine finishing off a wonderful day with sunset views and a handcrafted plate of scallop linguini, firecracker shrimp, or a good bowl of creamy lobster bisque. Water Street Cafe is another local favorite, offering a delicious menu filled with regional flavors. Try the seared yellowfin tuna, escargot pot pie, or braised salmon. All dishes at Water Street Cafe are crafted to perfection. The restaurant also offers non-seafood dishes, such as chili, skillet chicken, tofu, and a burger for guests craving other specialties.
Old Saybrook
Founded in 1635, Old Saybrook is a historical marvel and one of Connecticut's oldest towns. Step back in time at the General William Hart House, one of the first dwellings in Old Saybrook. What started as a family home in 1767 is now a museum. Delve into numerous exhibits showcasing old-time artifacts such as vintage clothing, lighting sources, furniture, portraits, and family heirlooms. Enjoy a "live story" at Fort Saybrook Monument Park. The vast open space contains panels that depict Fort Saybrook's rich heritage. Kick back as the area has stunning views of the Connecticut River and is fantastic for birdwatching.
The waterfront town boasts some breathtaking natural landscapes. Old Saybrook is a hotspot for fishing and boating. Rent a yacht, fishing boat, or other water explorer through Sailo to discover Connecticut's coastal beauty. Soak up some sunlight at Harveys Beach, a striking white sand beach known to be one of Connecticut's best. With lifeguards, washrooms, a playground, accessible grounds, and a snack stall, it is easy to see why Harvey's Beach is a fan favorite.
Washington
Washington is a little-known wonder in Litchfield County, snuggled by the Berkshire Mountains. This charming small town is home to many adorable small shops. Pick up a new title at The Hickory Stick Bookshop. Browse through books for all ages and genres or catch an event such as a book signing, virtual storytime, or join the book club. Enjoy a delicious breakfast, lunch, or snack at The Po Cafe. Choose from a carefully curated menu including vegan and gluten-free dishes. From sandwiches and soups to cookies and apple rings, the eatery strives to use fresh and local ingredients. Marty's Cafe is another area favorite, open seven days a week. Indulge in an afternoon panini, cappuccino, or iced pumpkin loaf to cap off the day in Washington.
Visit Washington during the autumn months to be surrounded by stunning warm hues and vibrant colors. The area is renowned for its fall foliage. While it is a gorgeous landscape year-round, Steep Rock Preserve is a phenomenal setting for soaking in those striking shades of reds, oranges, and gold that paint the landscape. The 998-acre region boasts numerous hiking trails showcasing Conneticut's elegant wilderness.
Kent
Kent is a scenic utopia perfect for photography and wanderlust. Snap a picture at the covered bridge by Bull's Bridge Scenic Area. Serving the area since 1842, the bridge is a notable Kent landmark. Kent Falls State Park is an essential stop featuring a hiking trail through a covered bridge toward the roaring cascading waterfall. To continue getting a hiking fix, Kent connects to the Appalachian Trail, where visitors can hike the iconic route in sections.
Everything is happening on Main Street Kent, from eclectic galleries to cozy cafes. The Morrison Gallery is an incredible way to spend a few hours. Browse through the striking collection of modern-style art pieces. The gallery is a top-rated attraction in Kent, and many visitors say the impressive works are a must-see. Afterward, stop at 45 on Main, a homey cafe specializing in coffee, chocolate, and ice cream. Each delicious delicacy is hand-crafted to perfection.
Wilton
Brimming with historical and well-preserved properties, Wilton is a charming New England town with a quiet atmosphere. There is no better way to dive into Wilton's rich past than by checking out the Wilton Historical Society. The museum complex features a variety of old-world buildings, ranging from the 1700s to 1800s, that are open for tours. Venture through a Blacksmith Shop, the Abbot Barn, and see the ever-changing exhibits at The Burt Barn Gallery and Sloan House Gallery. Continue exploring Wilton's roots by visiting the Weir Farm National Historical Park. Discover the former home of artist Julian Alden Weir and see the legacy of this American legend. The surrounding acreage is serene, radiant, and perfect for a stroll through Conneticuit's lush greenery.
Wilton's prosperous local offerings make the area a top choice for fresh produce. Browse and shop through an extensive list of vendors at the Wilton Farmer's Market. Open from June until the end of October, support the locals. Buy anything from hormone-free meats, natural candles, fresh bread, pasture-raised eggs, and naturally organic fruits and vegetables. Have a taste of Wilton's incredible farm-to-table creations at Baldanza at the Schoolhouse. The family-owned establishment is in an adorable old schoolhouse and offers fresh cuisine featuring locally sourced ingredients. Try the handmade ravioli, north Atlantic grey sole, or shrimp risotto.
Woodstock
Woodstock is the epitome of rural New England. Finish off the summer at the annual Woodstock Fair, Connecticut's largest agricultural fair. Join the locals on Labour Day weekend for live music, farm shows featuring livestock and horses, food, and a cornhole tournament. While Woodstock has a bevy of farms, Azuluna Farms stands out from the crowd. This circa 1700s farm graces around 200 rolling acres of stunning landscape and is one of the oldest buildings in the state. Hop on board an Amish-style cart and tour the farm while learning about the animals and farm operations.
As one of the original 13 colonies, Connecticut is loaded with historical sites showcasing the state's incredible heritage. See the beauty of Roseland Cottage, an 1846 Gothic-style masterpiece that served as a former summer home for the Brown family. Book a tour and venture around this incredibly remarkable piece of history. Roseland Cottage looks straight out of a fairytale, with a steeped roof, distinct pinkish exterior, stained glass windows, and a whimsical garden surrounding the enchanting residence. Since the 1800s, Woodstock Academy has stood tall and strong. Currently, it serves as a boarding and college preparatory school and is situated on Nipmuc Nation Native grounds. Historical tours of Woodstock Academy are available as per request.
Venture Off the Beaten Path and Explore Hidden Connecticut
Connecticut is a New England masterpiece that dazzles visitors with its striking collection of idyllic towns. Venture off the beaten path and explore some of the State's best-kept secrets. Have a quintessential fall vacation amongst the magazine-worthy fall foliage in Washington. Visitors to Roxbury can bask in the expansive wilderness amidst the rural backdrop. Ride the vintage steam train through Essex or explore countless historical landmarks in Wilton, Woodstock, and Old Saybrook. Those who wander to Connecticut will fall in love with the State's endless magic.
