10 of the Loveliest Lakeside Towns in Massachusetts

Here are 10 of the loveliest lakeside towns in Massachusetts, perfect for scenic getaways and lakeside relaxation:

1. Lakeville — Nestled between Assawompset and Long Ponds, Lakeville offers boating, fishing, and hiking in nearby Massasoit State Park. Its historic district adds charm to the lakeside atmosphere.​
2. Great Barrington — Known as Massachusetts’ most charming lakeside town, it features Lake Mansfield with beaches and parkland, combining rural charm with cultural attractions in the Berkshires.​
3. Edgartown — Located on Martha’s Vineyard, this picturesque town features historic streets, a lighthouse, and beautiful beach access, combining elegance with coastal lakeside vibes.​
4. Rockport — A quaint fishing village on the North Shore with colorful shops, art galleries, and waterfront promenades, known for the iconic Motif 1 fishing shack.​
5. Webster — Home to Lake Chaubunagungamaug (Lake Webster), one of Massachusetts’ largest natural lakes offering boating, fishing, and scenic beauty.​
6. Chatham — Located on Cape Cod’s “elbow,” Chatham features beaches, lighthouses, and quaint shops, perfect for a lakeside-inspired coastal experience.​
7. Gloucester — Famous for its fishing heritage, Gloucester also features great beaches and waterfront dining, offering lakeside ambiance with seaside charm.​
8. Falmouth — Another Cape Cod gem, Falmouth offers beautiful beaches such as Old Silver Beach along with quaint shops and museums.​
9. South Hadley — Home to Summit House, a historic mountaintop destination with breathtaking views of the Connecticut River, giving a lakeside experience from above.​
10. Winthrop — A small coastal town with scenic shore drives and views over the water, offering a peaceful lakeside-like retreat close to Boston.​

These towns combine natural lakeside or coastal water beauty with a mix of historic charm, outdoor activities, and family-friendly settings, making them top picks in Massachusetts for lakeside town exploration.

SOURCES

[1](https://www.worldatlas.com/cities/8-best-lakeside-towns-on-the-atlantic-coast.html)
[2](https://newenglandwanderlust.com/new-england-coast/)
[3](https://wupe.com/charming-lakeside-massachusetts/)
[4](https://www.tripadvisor.in/HotelsList-Massachusetts-Resorts-On-The-Lake-zfp29166958.html)
[5](https://theworldonmynecklace.com/best-small-towns-in-massachusetts/)