11 Best Lakeside Towns in Massachusetts
Massachusetts is shaped by water both inland and along the Atlantic. Glacial lakes fill the Berkshires, long recreational lakes run through Worcester County, and broad freshwater shorelines anchor towns from MetroWest to the South Coast. On Lake Quinsigamond in Shrewsbury, the shoreline paths stay busy with walkers from Dean Park and Lake Park. In Pittsfield, Lake Onota and Pontoosuc frame everyday stops between Park Square and places like District Kitchen & Bar.
Below are the best lakeside towns in Massachusetts; they are organized around lakes every season, and small downtowns sit minutes from the water.
Stockbridge
In western Massachusetts’ Berkshire County, Stockbridge sits by the Housatonic River in the Berkshire Hills about 12 miles south of Pittsfield. Named for a town in Hampshire, England, the Stockbridge Bowl (also called Lake Mahkeenac) is easily accessible, located just 2.5 miles north of the town. This 398-acre great pond is used year-round by swimmers, scullers, fishermen, waterskiers, kayakers, and powerboaters. To reach Lake Mahkeenac, Stockbridge residents can use the public boat ramp, the Town Beach on the Bowl’s southeastern corner, or rent canoes from Berkshire Outfitters.
Adding to the town’s tourism appeal is the Norman Rockwell Museum, featuring the world’s most extensive collection of original artworks by the American illustrator Norman Rockwell. Also not to be missed is Naumkeag, a National Historic Landmark District, the centerpiece of which is the Shingle Style 44-room country house within terraced gardens and landscaped grounds. Lodge at the Red Lion Inn on Main Street, purchase beautiful presents and artworks from the Whispered The Heart gift shop, and savor locally sourced American dishes at Once Upon a Table Restaurant.
Pittsfield
Berkshire County’s traditional county seat, Pittsfield, balances natural scenery with modern comforts, thanks to its setting around two major lakes: Lake Onota and Lake Pontoosuc. The 617-acre Onota Lake, located entirely within the community, offers many recreational opportunities, including swimming, sailing, fishing, jet skiing, and water skiing, as well as serving as a venue for the celebrated summer musical event ‘Live on the Lake.’ Pontoosuc Lake, straddling the boundary between Pittsfield and Lanesborough, attracts many kayakers, boaters, and water skiers, with large crowds on summer weekends.
The Colonial Theatre hosts theater productions and musicals throughout the year. The Berkshire Athenaeum, also known as the Pittsfield Public Library in Park Square, maintains a local history collection along with works and manuscripts by Herman Melville in the Herman Melville Memorial Room. Pittsfield State Forest has hiking and mountain biking trails, and the District Kitchen & Bar serves craft brews, cocktails, and seasonal American fare.
Shrewsbury
Christened after the English market town of Shrewsbury, this Worcester County settlement prospered from a primarily agrarian community to a suburban haven owing to its proximity to Worcester and Lake Quinsigamond. The 772-acre waterbody is a popular recreational spot, hosting high school and college rowing competitions and regattas, as well as fishing, boating, and picnicking.
History enthusiasts can tour the General Artemas Ward House, the long-term residence of the Revolutionary War General Artemas Ward, currently maintained as a museum by Harvard University. In the town center, Willy’s Steakhouse Grill & Sushi Bar serves dry-aged steaks and fresh sushi, whereas the Lakeside Bar & Grille in the Quinsigamond Plaza is fit for enjoying some classic pub menu in a cozy environment. Connect with locals through the diverse programs and services of the Shrewsbury Public Library, and visit 79-acre Dean Park for strolling, biking, and family outings.
Lakeville
Lakeville, a Plymouth County town dominated by a system of lakes, draws visitors with its small-town character, open-air recreations, and cultural offerings. The center of attention of Lakeville’s outdoor scene is the Assawompset Pond Complex, which includes the Assawompset Pond, Long Pond, and others, where water aficionados can participate in water-based activities.
For those seeking to escape the hubbub of Boston, Lakeville is a calm oasis, with the Fall Brook-Washburn Conservation Area and Massasoit State Park nearby, ideal for a balmy afternoon in a green space. The Greek Revival-style Old Town Hall is currently used as a community meeting space. The Lakeville Arts Council's annual Lakeville Arts & Music Festival celebrates the arts, handmade crafts, children’s activities, live music, and lots of food and drinks.
Monterey
Formally incorporated in 1847 as Tyringham and later named in commemoration of the Battle of Monterey, this Berkshire County town sits at the starting point of the Konkapot River in the southern extremity of the Berkshires. Located in the midst of softly curving hills and thick woods, the town’s focal point is Lake Garfield, a 275-acre crystal-clear lake with a public boat launch and a well-maintained beach, excellent for swimming, kayaking, paddleboarding, and fishing.
Guided tours of the Bidwell House Museum, a restored Georgian-era saltbox built in 1760, focus on colonial architecture and early settler life. The Roadside Store & Café is a gathering place for residents and visitors, serving breakfast sandwiches, flavored coffee, homemade treats made with local ingredients, and farm beef burgers for lunch. At Beartown State Forest, visitors can watch wildlife, ride horses, hike the 7.5-mile stretch of the Appalachian Trail, camp, and picnic.
Otis
Otis, a placid town situated at the southern tip of the Berkshire Mountains, is full of hills, lakes, forests, and community amenities. Central to Otis’s lakeside allure is the Otis Reservoir, a 1,065-acre water body known for boating, water skiing, snowmobiling, swimming, and both summer and winter fishing, thanks to a sizeable population of bass, yellow perch, catfish, trout, and tiger muskies. The Tolland State Forest, which circles the reservoir, has wooded campgrounds, forest trails for hiking, cross-country skiing, mountain biking, and off-road vehicles, and a day-use area for swimming and picnicking.
Within Otis, the Farmington River offers tubing, kayaking, paddling, as well as fishing for trout, carp, smallmouth bass, and sometimes salmon. The one-room East Otis Schoolhouse highlights the town’s rural roots, and the Knox Trail Inn serves comfort food in an intimate setting.
Great Barrington
Occupying the Housatonic River Valley, Great Barrington is a small Berkshire County town known for its natural setting. Travelers come to Great Barrington, especially attracted by the Lake Mansfield Recreation Area, which features a 29-acre pond and a juxtaposed 29-acre Conservation Forest with a quarter-mile smooth walking loop trail.
A popular spot for friends and families, the Lake Mansfield Recreation Area has open fields for picnics, swimming access to Lake Mansfield, walking trails, fishing, and nature watching. In the Great Barrington Cultural District, Artemesia sells handmade clothing and accessories, while Bear Butter serves almond butter smoothies and snacks. The Mahaiwe Performing Arts Center hosts live performances, film screenings, and family programs.
Webster
Webster is a Worcester County town near the Massachusetts-Connecticut border, known for Webster Lake, officially called Lake Chaubunagungamaug and often referred to by a much longer variant name. This 1,442-acre lake with a 17-mile shoreline, 7-8 islands, and two marinas, has the longest name among all geographic features in the US: Lake Chargoggagoggmanchauggagoggchaubunagungamaugg. Excursionists get to participate in boating, swimming, and bass tournaments organized by local groups. Memorial Beach offers unlimited public access, with sandy swimming areas and picnic and beach volleyball facilities.
The Indian Ranch on the shores of Webster Lake is a premier outdoor concert venue and campground that has been hosting live music since 1946. Apart from the music shows, a one-and-a-half-hour cruise aboard the ‘Indian Princess paddlewheel boat’ is perfect for lakeside panoramas and observing sunset during evening cruises. Learn about the town’s early education scenario at the restored District Five Schoolhouse, and at the Samuel Slater Museum, exhibits bring to life the chronicles of the American Industrial Revolution and its people.
Natick
In the heart of the state’s MetroWest region, this Middlesex County town, named from the language of the indigenous Massachusett tribe, is about 20 miles west of Boston. Created by the Lake Cochituate Dam’s construction, the 625-acre Lake Cochituate is used for water activities across its three linked ponds: North Pond, Middle Pond, and South Pond. Encompassing the three ponds of the lake is the day-use Cochituate State Park, where both town residents and tourists can partake in motor boating, canoeing, windsurfing, picnicking, kayaking, and swimming activities.
Downtown, the Natick Mall is a regular shopping destination, and Buttercup Restaurant serves farm-to-table cuisine in a contemporary setting. At The Center for Arts in Natick (TCAN), audiences can attend concerts by well-known musicians and bands, as well as film screenings, theatrical productions, open mic events, and a classical music series.
Shutesbury
Part of the Springfield Metropolitan Area, this rural community in northwestern Massachusetts’ Franklin County is known for its hills, woodlands, Lake Wyola, and the Quabbin Reservoir. Shutesbury's proximity to the Quabbin Reservoir, the state’s largest inland waterbody, ensures preservation of some of the town’s rustic character, as restrictions on development are in place within the Quabbin watershed.
In the northwestern corner of Shutesbury is Lake Wyola, a 128-acre lake offering swimming, fishing, boating, and picnicking, set against a backdrop of hills and forests. Also known as Carroll A. Holmes Recreation Area, Lake Wyola State Park is a day-use area on the shores of Lake Wyola, with a public boat launch, picnic area, restrooms, charcoal grills, and a volleyball court. Learn about the town’s history at South School, the iconic one-room schoolhouse, and other time-honored landmarks like the Shutesbury Old Town Hall at the heart of the town.
Sharon
A Norfolk County town, roughly 24 miles southwest of Downtown Boston, Sharon mixes deep history with a lively community spirit around its popular attraction, Lake Massapoag. This 392-acre, spring-fed lake is a favorite for sailing and sailboarding activities. Along the lake, Memorial Park Beach is ideal for summer swimming, picnicking, and the yearly Fourth of July celebrations, featuring a spectacular fireworks display over the lake. Just a short distance from Memorial Park Beach, the family-run Ward’s Berry Farm invites tourists to buy gourmet grocery items and prepared foods from the farm store, pick-your-own crops, and enjoy hayrides throughout the pick-your-own season.
In the National Register-listed Sharon Historic District, walk past local landmarks such as the Greek Revival-style Unitarian Church and the 1753-built Dennett House, the district’s oldest building. Also, engage in nature walks, bird-watching, and hiking the over 20 miles of trails at the Massachusetts Audubon Society’s oldest and largest wildlife sanctuary, Moose Hill.
From Lake Mahkeenac in Stockbridge to Lake Quinsigamond in Shrewsbury, these lakes and towns offer distinct experiences in the Bay State. Whether planning a weekend trip or considering a move, these 11 lakeside locales, highlighting the best of what Massachusetts has to offer, are worth a visit.
