Nine Best Lakeside Towns in Connecticut
New England is world-famous for its abundance of sprawling lakes and reservoirs, and Connecticut does not disappoint. Some of the most scenic towns in Connecticut provide direct access to the largest lakes in the state, like Bantam Lake in Litchfield or Candlewood Lake in Sherman. In smaller towns like Chester or Salisbury, you will be completely surrounded by lush foliage while swimming through Twin Lakes or the Pattaconk Reservoir. And if you like adventure, you will be pleased to learn that the lakes in Kent and Oxford are accompanied by exhilarating trails and jaw-dropping mountain views. On that note, the following towns showcase the very best of Connecticut's natural landscape, making them solid choices for a relaxing weekend.
Litchfield
Widely viewed as the quintessential rural New England village, Litchfield's picturesque downtown is decorated with historic architecture, towering trees, eccentric shops, and acclaimed restaurants like West Street Grill, hailed for its upscale New American cuisine.
At the Market Place Tavern, guests can dine in a building that once housed prisoners during the War of 1812.
During the warmer months, visitors flock to Morris Town Beach and Sandy Beach, both located just ten minutes from downtown and major hubs for swimming, sailing, and fishing in Bantam Lake, Connecticut's largest natural lake.
For a gentle walk through nature, check out the Little Pond Boardwalk Trail, a 1.2-mile wooden walkway into a dense forest and a soothing wetland. If you visit in the spring, you won't want to miss the Laurel Ridge Daffodil Fields, where you can view more than 15 acres of freshly bloomed white and yellow flowers.
Sherman
Sherman is perched on the northern edge of Candlewood Lake, a man-made reservoir and the largest lake in Connecticut. It makes sense to visit Sherman if you know someone from the area, because though Sherman Town Beach Park provides access to Candlewood Lake, it's only open to residents and their sponsored guests.
However, Candlewood Lake is far from the sole outdoor attraction in Sherman. This town in the Housatonic Valley is also an entranceway to the Appalachian Trail, and you can even see the lake during your hike.
Additionally, the Wimisink Preserve offers a peaceful journey through a 55-acre freshwater wetland that serves as a habitat for a myriad of rare birds.
After a long day of walking, kick back with a glass of sparkling red raspberry wine at White Silo Farm and Winery. If you arrive for a tasting on an early Saturday or Sunday, you'll be welcomed with a warm pastry and a cup of local organic coffee.
Kent
A short drive from Kent, Lake Waramaug State Park offers access to Connecticut’s second-largest natural lake. Before you go for a swim, the forested drive around the lake is a visual goldmine in itself.
When you are in the mood for exercise, head to Macedonia Brook State Park and take the trail up to Cobble Mountain, culminating in panoramic views of the Catskill and Taconic Mountains. Less experienced hikers might prefer the much easier path to Kent Falls, a series of waterfalls that plunge 250 feet into the rushing Housatonic River.
Another great place to spend the day is Kent Barns, a complex of historic barns housing shops like RT Facts, providing an exceptional collection of luxurious antiques, sculptures, and custom-made furniture. Kent Barns is also where you'll find Ore Hill, a tasting menu-focused restaurant in a casual but intimate tavern setting.
New Milford
New Milford's historic downtown appears to have come out of a fairy tale, so it's no surprise that it was used in the 2002 RomCom Mr. Deeds. Hence, visitors typically begin their trips by exploring the New Milford Town Green, one of the longest grassy spaces in the state and framed by luxurious Victorian homes, bustling restaurants, and historic buildings like the Greek Revival-style Village Center for the Arts, originally constructed in 1830, and the First Congregational Church of New Milford.
New Milford is also located at the tip of Candlewood Lake, where visitors can swim at the immaculately maintained Lynn Deming Park, featuring a sandy beach and an expansive shaded picnic area.
If this scenery wasn't gorgeous enough, the historic bridge of Lovers Leap State Park rewards hikers with striking elevated views of the Housatonic Gorge and yet another massive body of water: Lake Lillinonah, Connecticut's second-largest lake.
Salisbury
Located at the top left corner of Connecticut near the border with New York, Salisbury is the proud home of Bear Mountain, the highest peak in the state. If you don't have the time to reach the 2,316-foot summit, the views from Lion's Head Trail are similarly stunning, and it's less than an hour to the top.
Visitors can cool off at the serene Twin Lakes of Lake Washining and Lake Washinee, a.k.a. West Twin Lake and East Twin Lake. The Twin Lakes are kept remarkably clean by the Twin Lakes Association, since both lakes are crucial freshwater sources for the state of Connecticut and a habitat for many endangered species.
When dinnertime rolls around, the restaurant at The White Hart Inn offers a sophisticated farm-to-table experience centered on classic dishes like steak, seafood, and pasta in a Colonial-era taproom.
Chester
Chester's downtown center isn't as big as Litchfield's or New Milford's, but it packs a full day's worth of activities into a small corner of the Connecticut River hillside.
After grabbing a coffee and a hearty breakfast at Three Fates on Main Street, you will have plenty of energy to peruse Chester's numerous galleries nearby, such as Leif Nilsson Spring Street Studio and Gallery or Lori Warner Studio/Gallery.
Meanwhile, the blue-blazed Cockaponset Trail in Cockaponset State Forest passes Pattaconk Reservoir, which has a seasonally monitored swimming area.
Tired from their outdoor adventures, hikers and swimmers often converge at the Little House Brewing Company, located in a 200-year-old building and specializing in brightly colored New England IPAs.
Oxford
Oxford is an affluent community known for its plentiful parks, trails, and lively craft breweries. Jackson Cove Town Park, for example, is located on Lake Zoar, a reservoir spanning 10 miles. Visitors can swim in Lake Zoar at Jackson Cove's secluded beach or take a challenging waterfront hike along the Oxford Loop of the Blue-Blazed Pomperaug Trail.
If you would prefer a less strenuous walk, Southford Falls State Park offers an easy path to a multi-tiered waterfall, a tranquil pond, and a historic red covered bridge that looks anything but dated against the surrounding wooded scenery.
As any beer aficionado will tell you, there is nothing like a cold blonde ale after a hike, and that is why Black Hog Brewing is one of Oxford's most popular local hangouts. This award-winning brewery features a diverse selection of brews, as well as an outdoor seating area with food trucks and cornhole courts.
Lastly, Rich Farm Ice Cream has been wowing visitors with its locally made ice cream since 1994, so it's certainly worth a visit.
Winchester
Nestled in the Litchfield Hills region of the southern Berkshires, Winchester and its Highland Lake are a prime spot for lakeside living as well as aquatic activities like boating, swimming, and fishing.
Alternatively, the much smaller Winchester Lake is more ideal for a quieter day on the water in the company of fascinating wildlife such as herons and ospreys.
Winchester also lays claim to one of the largest indoor collaborative art projects in the country, in the American Mural Project. Set in a former mill complex, this 120-foot-long, five-story-high mural provides a visual history through the lens of American farmers, construction workers, miners, ironworkers, and more.
Entertainment awaits at Little Red Barn Brewers, which supplements its vast food and drink menu with a regular schedule of live music and festive celebrations like the annual Oktoberfest, featuring a fun-filled stein-holding competition.
East Haddam
If you Google East Haddam, you will instantly be greeted with images of Gillette Castle State Park. Every year, hundreds of thousands of tourists visit this 14,000-square-foot, medieval-style stone castle overlooking the Connecticut River, designed by stage actor and playwright William Gillette and riddled with mind-bending features like hidden doors, built-in couches, and puzzle-like locks.
At East Haddam Town Beach, visitors can swim in the shallow, crystal clear waters of Moodus Reservoir.
When you are in the mood for some exercise, Devil's Hopyard State Park contains a large network of hiking trails for all experience levels, as well as the awe-inspiring Chapman Falls, a 60-foot cascading waterfall that drops into a deep pool in the Eightmile River.
If you are a fan of musicals, you definitely won't want to miss a show at the Goodspeed Opera House, a Victorian theater built in 1876 that continues staging productions year-round. Most recently, the theater hosted the premiere of their new musical, The Snow Goose.
Lakeside Adventures Await
Connecticut's lakeside towns offer an immersive escape into nature, where you can walk in absolute silence for hours before feasting your eyes on unbelievable views of the surrounding countryside.
Whether you are hiking the Appalachian Trail in Sherman, climbing up Bear Mountain in Salisbury, or gazing into the tallest waterfall in the state in Kent, each town offers its own brand of relaxation.
When you are not hiking or swimming, you are strolling through storybook downtown centers dotted with historical architecture and enough shops and restaurants to have your days and nights fully booked. So, if you are mulling over potential destinations for your next lakeside vacation, consider the unique attractions of these towns, and you will see what makes Connecticut a truly special part of the United States.
