8 Best Lakeside Towns in Connecticut
Connecticut may be one of the smallest states in the U.S., but its scenic towns pack a punch when it comes to charm, natural beauty, and outdoor adventures. From the largest natural lake at Bantam in Litchfield to the man-made marvel of Candlewood Lake in Sherman, these waterside havens offer abundant charm and adventure. Picture yourself kayaking on the serene Twin Lakes in Salisbury, hiking through the lush trails of Winchester, or soaking in the historic ambiance of East Haddam. Each town on this list provides a unique glimpse into Connecticut’s vibrant landscapes and past, making them perfect destinations for outdoor enthusiasts, history buffs, and anyone seeking lakeside tranquility.
Litchfield
Tucked in the beautiful Litchfield Hills, this charming town is home to Bantam Lake, the largest natural lake in Connecticut. Bantam has two gorgeous beaches to explore: Morris Town and Sandy Beach. Both offer a serene locale for sunbathing and relaxing along the lake's waters. For a more in-depth experience, one can sail or canoe in warmer months or try ice fishing and ice boating in winter. Much of the lake is protected by the nearby White Memorial Conservation Center, which has over 35 miles of hiking trails, including the popular Little Pond Boardwalk Trail. Visitors can also enjoy birdwatching, picnicking, mountain biking, horseback riding, and exploring the center's educational exhibits. Meanwhile, history enthusiasts love to explore the Topsmead State Forest, which has housed the former estate grounds of Miss Edith Morton Chase since 1929.
Morris
Morris is another lakeside Connecticut town near Bantam Lake. Located on the southern shore, it has access to all the lake has to offer. Swim in the cool waters or adventure through the lush wetlands. The region is known for its rich farmlands. Visit Sunset Meadow Vineyards for wine tasting, or check out the farm-turned-event space White Barn at South Farms. White Flower Farms is another must-see. Dating back to the 1950s, it covers ten acres with beautiful gardens and floral displays. For some more outdoor scenery, Camp Columbia State Park and Forest is a short drive away. The park has changed over the years from a farm to a higher education campus and is now open land with hiking trails.
Kent
Kent is a dream for those who love nature, thanks to the sparkling waters of Lake Waramaug. Access the lake via Washington Town Beach for swimming and boat rentals. Fishers with permits can try their hand at catching big and small-mouth bass, pickerel, yellow perch, bullhead, and sunfish. Camping is available in the state park. Another great option is Kent Falls State Park, which has stunning waterfalls. The Kent Falls Steps Trail leads to breathtaking vistas of the 250-foot waterfall and Housatonic River. Furthermore, Macedonia Brook State Park has even more hiking trails with rugged terrain, and you can enjoy seasonal vibrant autumn colors. For some history, don’t miss the former home of local author, artist, and illustrator at the Eric Sloane Museum and Kent Furnace.
New Milford
New Milford is a town in Connecticut that looks right out of a storybook. Its proximity to Candlewood Lake adds natural beauty to its charm. Candlewood Lake is a popular spot for boating, jet skiing, and fishing. Lynn Deming Park has sandy beaches and picnic areas where you can relax on a day by the water. Similarly, Lovers Leap State Park has trails with amazing views of the Housatonic River Gorge and the Lovers Leap Bridge.
After the outdoor fun, head back to the town center, where Main Street is a hub for farmers' markets and concerts, creating a lively atmosphere. In August, the Jazz on the Green musical series fills warm evenings, while colder months host the Sip and Stroll in the historic Downtown.
Sherman
Sherman also sits on the edge of Candlewood Lake, north of Housatonic Valley. The town shares its border with New York State, making it an excellent option for those traveling from NY or larger cities. Those here for the waterside charm should swim or kayak at the lovely Sherman Town Beach. For a different outdoor experience, the Appalachian Trail offers scenic hikes featuring the lake. On the other hand, head back into town to visit the White Silo Farm & Winery for some wine. After a drink, the Sherman Playhouse Theater is a great place to watch a musical or play. Before leaving, check out The Old Store Gift Shop & Museum to learn more about the region's roots and grab some souvenirs.
Winchester
Winchester, nestled in the picturesque Litchfield Hills, is a lakeside gem perfect for a serene getaway. Highland Lake, a three-mile-long haven for boating, anglers, and summer regattas, offers lively fun. Outdoor enthusiasts can rent boats at Highland Lake Marina or relax by its sparkling waters. At the same time, the quieter Winchester Lake is ideal for kayaking and spotting wildlife such as herons, ospreys, and turtles.
The town’s historic charm shines in Winsted, its downtown hub, where visitors can explore antique shops, artisan studios at Whiting Mills, and late 19th-century architecture. For unique experiences, the American Museum of Tort Law provides an educational twist, while the Gilson Café & Cinema pairs dinner with a movie or live music. After a day of adventures, grab a craft brew at the Little Red Barn Brewery.
Salisbury
Salisbury, nestled near the serene Twin Lakes, is a paradise for outdoor enthusiasts and nature lovers. Twin Lakes—comprising Washinee and Washining—offer excellent canoeing and birdwatching opportunities, with species such as waterfowl, sparrows, and bald eagles often spotted along the shores. For hikers, the Lion’s Head Trail rewards them with sweeping views of the rolling countryside from its summit.
The town comes alive each winter with the annual ski jump competition hosted by the Salisbury Winter Sports Association, a thrilling event that draws spectators from near and far. Beyond the outdoors, Salisbury charms with its local shops and eateries. Grab a bite at the charming Sweet William’s Coffee Shop & Bakery, browse treasures at The Salisbury General Store and Gifts, or enjoy a locally sourced meal at The White Hart Inn.
East Haddam
East Haddam, perched along the scenic Connecticut River, offers a perfect blend of outdoor adventures and cultural attractions. Moodus Reservoir and Lake Hayward are popular spots for kayaking, fishing, and peaceful days on the water. Nature enthusiasts will love Devil’s Hopyard State Park, home to the striking Chapman Falls and miles of hiking trails through lush woodlands.
For a dose of history and whimsy, visit Gillette Castle State Park. The eccentric mansion of actor William Gillette overlooks the river, complete with stone archways, secret doors, and breathtaking views. The town’s vibrant cultural scene shines at the Goodspeed Opera House, an iconic theater that stages Broadway-caliber musicals year-round.
Wrapping Up
Connecticut’s lakeside towns are more than just destinations—they’re invitations to explore, unwind, and connect with the beauty of nature. From the historic charm of East Haddam to the wildlife-rich waters of Winchester, each town boasts its own story, blending natural splendor with cultural appeal. Whether you’re paddling on Twin Lakes in Salisbury or hiking the Appalachian Trail in Sherman, these lakeside escapes capture the heart of what makes Connecticut unique. Next time you crave a retreat filled with scenic views and memorable moments, let these charming towns guide you to lakeside serenity.
