I’m a sucker for New England. I’ve been a number of times and will definitely go again. I’ve road-tripped extensively throughout the region zig zagging in my car enjoying so many scenic small towns both inland and on the ocean. I was particularly taken by so many quaint lakeside towns; normally one thinks of the ocean when talking about New England but there are so many great lakes in the region with wonderful towns. This was not an easy list to put together just because there were so many options but I managed to whittle it down to 25 towns.
18. Greenville, Maine
Located on the southern tip of Moosehead Lake, Greenville is a small, scenic town surrounded by the wilderness of Maine. Moosehead Lake is the largest in the state, offering kayaking, fishing, and wildlife watching—particularly moose. Greenville’s quaint downtown features local cafes, small inns, and outfitters for outdoor adventures. Nearby, Mount Kineo offers one of the best hikes in the area, with stunning views of the lake from its summit. Greenville’s peaceful atmosphere and lakeside beauty make it a top nature getaway.
17. Bridgton, Maine
Set on the shores of Highland Lake, Bridgton is a small town with a history dating back to the 18th century. The town is a popular destination for boating, fishing, and swimming, with beautiful mountain views reflected in the calm waters of the lake. Bridgton’s charming Main Street offers a mix of antique shops, galleries, and cozy cafes. Pleasant Mountain, just a short drive away, provides hiking opportunities with scenic overlooks of the lake. Bridgton’s blend of outdoor adventure and small-town charm make it a perfect lakeside destination.
16. Meredith, New Hampshire
Meredith, located on the northwestern shore of Lake Winnipesaukee, is known for its scenic beauty and historic mill buildings. The town’s Mill Falls Marketplace offers boutique shopping and local dining, while the lake itself is a hub for boating, swimming, and kayaking. Visitors can take a boat ride on the historic M/S Mount Washington or enjoy scenic views from Bear Island. Meredith’s picturesque downtown, combined with its lakeside activities, makes it a popular spot for summer travelers.
15. Laconia, New Hampshire
Laconia sits between Lake Winnipesaukee and Lake Winnisquam, offering plenty of lakeside activities like jet skiing, boating, and swimming. The town’s historic downtown has charming shops, cafes, and a local diner. Laconia is also home to Weirs Beach, a popular destination for families, and the Laconia Motorcycle Week, one of the oldest bike rallies in the U.S. With its fun lakeside attractions and New England charm, Laconia is a perfect summer getaway.
14. Rangeley, Maine
Perched on the shores of Rangeley Lake, this charming town is an outdoor paradise in western Maine. Rangeley Lake is perfect for boating, fishing, and kayaking, with stunning views of the surrounding mountains. The quaint downtown features local cafes, art galleries, and shops that cater to outdoor enthusiasts. Rangeley Lakes Heritage Trust maintains trails for hiking and birdwatching, while the nearby Saddleback Mountain offers excellent skiing in winter. Rangeley’s scenic beauty and outdoor activities make it a top destination for nature lovers.
13. Holderness, New Hampshire
Nestled along the shores of Squam Lake, Holderness is a peaceful and picturesque lakeside town. Squam Lake, famous for being the filming location of On Golden Pond, offers boating, kayaking, and excellent fishing. The town’s small downtown features local shops, cafes, and inns. Visitors can explore Squam Lakes Natural Science Center, which offers nature trails and wildlife exhibits. Holderness is perfect for those looking for a quiet, serene escape into nature.
12. Stowe, Vermont
While known for its ski resorts, Stowe also offers access to the serene waters of Waterbury Reservoir. The lake is ideal for kayaking, paddleboarding, and fishing against a backdrop of Vermont’s Green Mountains. Stowe’s downtown is charming, with historic inns, local eateries, and boutique shopping. The nearby Stowe Recreation Path offers scenic biking and walking trails that meander through forests and meadows. Stowe’s mix of outdoor adventure and quaint New England charm makes it a great lakeside destination, especially in summer.
11. Westport, Connecticut
Located on Long Island Sound, Westport is a quaint coastal town with access to calm waters perfect for boating and fishing. The town’s historic downtown is filled with unique shops, galleries, and farm-to-table restaurants. Compo Beach is a local favorite for swimming and picnicking, while Sherwood Island State Park offers hiking trails and scenic views of the sound. Westport’s charming colonial architecture and relaxed beach atmosphere make it a great lakeside retreat. of the lakes.
10. Greensboro, Vermont
Greensboro is a small, artsy town on the shores of Caspian Lake, a clear and peaceful lake perfect for swimming, canoeing, and fishing. The town is known for its scenic beauty and local arts scene, with The Highland Center for the Arts hosting events throughout the year. Greensboro’s downtown features local shops, a farmstand, and an old-fashioned general store. Nearby, visitors can hike Barr Hill Natural Area for panoramic views of the lake and surrounding hills.
9. Belgrade Lakes, Maine
Belgrade Lakes is a small town nestled between Great Pond and Long Pond in central Maine. Both lakes are known for their excellent boating, fishing, and swimming opportunities, and the town itself exudes classic New England charm with its local shops, inns, and restaurants. Visitors can play a round of golf at the Belgrade Lakes Golf Club, rated as one of the best in the U.S. The town’s scenic setting and relaxed atmosphere make it a peaceful retreat.
8. Sunapee, New Hampshire
Sunapee is a quintessential New England town located on the shores of Lake Sunapee. The lake is ideal for boating, sailing, and swimming, with a marina offering boat rentals. Sunapee Harbor is particularly charming, with small shops, cafes, and ice cream stands along the water’s edge. Nearby, visitors can hike Mount Sunapee or enjoy skiing in the winter. Sunapee’s scenic lakeside setting and year-round activities make it a perfect New England retreat.
7. Middlebury, Vermont
Located near Lake Dunmore, Middlebury is a historic college town with a charming downtown filled with 19th-century buildings and local shops. Lake Dunmore offers excellent opportunities for boating, fishing, and swimming, while nearby Branbury State Park provides scenic hiking trails and picnic areas. Middlebury’s downtown is home to the historic Middlebury College, as well as art galleries, cafes, and restaurants. The town’s blend of history, academia, and lakeside beauty make it a perfect destination for a relaxing escape.
6. Pittsfield, Massachusetts
Located near Onota Lake and Pontoosuc Lake, Pittsfield is a historic town in the Berkshires offering a rich cultural scene and scenic lakeside beauty. Both lakes are popular for boating, fishing, and kayaking, with picnic areas and scenic spots for relaxation. Pittsfield’s downtown is filled with historic buildings, art galleries, and cultural venues, including the famous Colonial Theatre. The town’s proximity to Tanglewood, the summer home of the Boston Symphony Orchestra, adds to its cultural appeal.
5. Litchfield, Connecticut
Litchfield, located near Bantam Lake, is one of Connecticut’s most charming and historic towns. Bantam Lake is the largest natural lake in the state and offers plenty of opportunities for boating, kayaking, and fishing. The town’s quaint downtown is lined with colonial-era buildings, housing local shops, cafes, and the Litchfield Historical Society, which offers insights into the town’s rich Revolutionary War history. Nearby, White Memorial Conservation Center provides miles of scenic hiking and wildlife viewing opportunities. Litchfield’s blend of history, outdoor beauty, and New England charm make it a perfect lakeside destination.
4. Castleton, Vermont
Situated on the shores of Lake Bomoseen, Castleton is a small, picturesque town steeped in history and natural beauty. Lake Bomoseen, Vermont’s largest lake, is perfect for boating, swimming, and fishing, and offers stunning views of the surrounding mountains. Castleton’s historic downtown features 19th-century buildings, cozy bed-and-breakfasts, and the scenic Castleton University campus. Visitors can also explore the nearby Bomoseen State Park, which provides hiking trails and picnic areas. Castleton’s peaceful lakeside setting and historic charm make it an ideal spot for a relaxing retreat.
3. Wolfeboro, New Hampshire
Known as the “Oldest Summer Resort in America,” Wolfeboro sits on the shores of Lake Winnipesaukee. This quintessential New England lake town offers boating, sailing, and fishing on the state’s largest lake. The charming downtown is filled with local restaurants, boutiques, and bed-and-breakfasts. Visitors can explore the Wright Museum of WWII or take a scenic boat tour on the M/S Mount Washington. Wolfeboro’s colonial architecture and relaxed lakeside vibe make it a perfect summer retreat.
2. New London, New Hampshire
New London, New Hampshire, is a picturesque lakeside town nestled between Pleasant Lake and Little Sunapee Lake, offering stunning waterfront views and tranquil surroundings. The town’s charm lies in its blend of historic New England architecture, scenic landscapes, and a tight-knit community. Outdoor enthusiasts can enjoy boating, fishing, and swimming in the lakes during the summer, while nearby Mount Sunapee provides hiking and skiing opportunities year-round. The town’s quaint downtown features boutique shops, local cafes, and cultural events, fostering a welcoming small-town atmosphere. With its natural beauty and peaceful lifestyle, New London is an ideal place for those seeking a serene lakeside retreat.
1. Newport, Vermont
Located on the southern shores of Lake Memphremagog, Newport offers stunning lake views and a charming downtown filled with Victorian architecture. Lake Memphremagog is perfect for boating, fishing, and kayaking, with easy access to the Canadian border. Newport’s downtown features local shops, restaurants, and cafes, making it a perfect place to relax after a day on the water. The town is also close to Jay Peak, which offers skiing in winter and hiking in summer.
