8 Best Lakeside Towns in Massachusetts

When most people think of Massachusetts, their minds drift to coastal clam shacks, Revolutionary War landmarks, or the storied streets of Boston. But hidden away from the Atlantic’s salty breeze lies another side of the Bay State: its idyllic lakes and the welcoming towns lining their shores.

Many of these inland gems boast a fascinating mix of colonial roots and modern-day allure where you might stumble upon a centuries-old mill, only to discover a hip lakeside café down the road. In this article, we’ll shine a light on eight of the best lakeside destinations in Massachusetts, each offering a fresh slice of New England magic far from the beaten coastal path.

Stockbridge

Stockbridge stands in the southwestern corner of Massachusetts, in the Berkshires. The town was incorporated in 1739 and hosted historical figures such as Norman Rockwell, whose artworks are displayed at the Norman Rockwell Museum. Lake Mahkeenac, also called Stockbridge Bowl, lies just north of town and supports swimming, fishing, and sailing. Naumkeag, a National Trust Historic Site, showcases formal gardens and architectural design. The Red Lion Inn on Main Street has been in operation since 1773 and offers lodging. The town maintains a compact layout with accessible sidewalks and preserved buildings.

Lake Mahkeenac is best accessed through the Stockbridge Town Beach on Hawthorne Road. Kayakers often explore its shoreline. Visitors may purchase canoe rentals from Berkshire Outfitters and follow posted fishing guidelines. The Berkshire Botanical Garden hosts horticultural exhibits and educational programs. The Mission House, an 18th-century building, contains Indigenous artifacts. The Stockbridge Library, Museum & Archives features local genealogical records. Local dining options include the Main Street Café, known for its breakfast menu, and Once Upon a Table, which offers lunch and dinner.

Otis

Otis is also situated in the Berkshires, known for the Otis Reservoir, the state's largest recreational body of water. Established in 1810, Otis is a small town that provides an ideal setting for relaxation and nature activities. The reservoir attracts enthusiasts of kayaking, boating, and fishing, catering to both summer and winter fishing due to its abundant population of bass, pickerel, and perch. Nearby, Tolland State Forest offers extensive hiking trails and camping facilities, providing direct access to the lake's shoreline.

Within Otis, the Farmington River provides additional opportunities for outdoor sports, particularly fly fishing and white-water rafting, managed by companies such as Berkshire Fishing Adventures. The Knox Trail Inn stands out as a popular local dining spot, offering traditional American cuisine with views of the surrounding landscapes. For cultural experiences, the Otis Ridge, a small but historic ski area, provides winter sports opportunities. Additionally, the Otis Poultry Farm, although primarily a store, is a local landmark offering fresh, local produce and goods, illustrating the town's connection to its rural roots and community-focused lifestyle.

Monterey

Monterey, another Berkshires's gem, was incorporated in 1847. This town, small in size but rich in history, is closely tied to Lake Garfield, a central hub for residents and visitors. The lake is well-equipped for swimming, with a public beach that is meticulously maintained for summer visitors, and offers boat ramps for those looking to fish or casually paddle. Winter activities include ice fishing, reflecting the year-round appeal of the area. The Bidwell House Museum, a meticulously restored 18th-century homestead, provides historical insights through guided tours, highlighting the town's colonial roots.

Socially, Monterey facilitates a close-knit community atmosphere at places like the Roadside Cafe, a favorite for locals seeking hearty breakfasts and lunches. For outdoor enthusiasts, Beartown State Forest offers extensive hiking trails and picnic areas, enhancing Monterey's appeal as a destination for those seeking both relaxation and adventure in a serene lakeside setting.

Pittsfield

Pittsfield, the largest city in the Berkshires of Massachusetts, balances urban offerings with appealing natural settings, particularly Onota Lake and Pontoosuc Lake. Pittsfield's historical significance is marked by its establishment in 1753 and its role in the American Revolution. Onota Lake serves as a recreational focal point, facilitating boating, swimming, and fishing, with Pontoosuc Lake offering similar amenities plus winter sports like ice fishing. The Berkshire Athenaeum adds cultural depth to the city, hosting a comprehensive collection of Herman Melville memorabilia, which connects to the author’s nearby home.

The city's vibrant cultural scene is bolstered by institutions like the Barrington Stage Company and the Colonial Theatre, which provide high-quality theatrical productions year-round. For dining, the bustling District Kitchen & Bar, known for its craft cocktails and American dishes. The Pittsfield State Forest offers extensive trails for hiking and mountain biking, contributing to the city's appeal for those seeking both cultural enrichment and outdoor adventure in a picturesque lakeside setting.

Shrewsbury

Shrewsbury is a town that effectively combines its historical heritage with modern amenities, positioned just east of Worcester and incorporating part of Lake Quinsigamond. Founded in 1727, Shrewsbury has evolved from a largely agricultural community to a suburban haven with noteworthy historical sites such as the Artemas Ward House, a museum dedicated to the Revolutionary War general. Lake Quinsigamond is a key recreational site, hosting collegiate and high school rowing competitions, and providing facilities for boating and fishing.

The town center features a blend of dining and retail options. Willy's Steakhouse Grill & Sushi Bar offers a high-end dining experience, while Lakeside Bar and Grille provides a casual atmosphere with views of Lake Quinsigamond. For family-friendly activities, the Dean Park is a popular destination offering playgrounds, tennis courts, and scenic picnic areas. The Shrewsbury Public Library, recently renovated, serves as a community hub, offering a range of programs and services that enhance local engagement and education.

Webster

Webster, positioned near the Connecticut state line, is notable for its expansive Webster Lake, formally known as Lake Chargoggagoggmanchauggagoggchaubunagungamaugg, the lake with the longest name in the United States, often celebrated for its Algonquin heritage. The town, incorporated in 1832, leverages its lakeside setting by offering plentiful water-based activities such as swimming, boating, and fishing, particularly noted for its bass tournaments. Memorial Beach provides public access with facilities for picnics and beach volleyball.

Cultural and dining venues in Webster include Indian Ranch, a unique concert venue hosting popular musical acts with a scenic lakeside backdrop. For dining, Point Breeze, a restaurant located directly on the lake, offers seafood and American cuisine with views of the water. The French River Park, a recent addition to the town, provides walking trails and picnic spots along the river, enhancing Webster’s commitment to outdoor spaces. The town’s annual events, like the Indian Princess paddlewheeler cruises, draw visitors and locals alike.

Great Barrington

Great Barrington, located in the southern part of the Berkshires in Massachusetts, has a rich history that includes being an early center for the civil rights movement; it was the first town in the U.S. to elect an African-American to office in 1841. Lake Mansfield, a small yet vital part of this community, offers swimming, boating, and fishing, enhancing the town’s appeal. The lake has a well-maintained public beach and a trail surrounding it that is popular for walks and nature observation. The Mahaiwe Performing Arts Center stands as a cultural beacon in the town, offering year-round events including concerts, films, and theater productions.

Downtown Great Barrington is known for its vibrant main street, which features a variety of boutiques, restaurants, and cafes. Rubiner's Cheesemongers & Grocers offers gourmet foods and cheeses.

Natick

Natick, positioned just 20 miles west of Boston, was established in 1651 and has evolved into a significant cultural and commercial hub. The town is named after the local Native American tribe and means "place of hills". Lake Cochituate in Natick offers a variety of water-based activities including swimming, boating, and fishing across its three sections: North, Middle, and South Ponds. Cochituate State Park, located along the lake's shores, provides facilities for picnicking and a boat ramp, making it a popular destination for both residents and visitors.

Downtown Natick contributes to its charm with a range of local businesses and eateries. The Buttercup restaurant features farm-to-table dining. The Center for Arts in Natick (TCAN) serves as a cultural focal point, offering live performances and film screenings. Additionally, the Natick Mall, the largest shopping mall in New England, offers extensive retail options and dining.