Top 15 Activities and Attractions in Weston, MA

A residential western suburb of Boston, Weston is appreciated for its pastoral ambiance, with over 2,000 acres designated as conservation areas and public parks.

The town’s civic center emerged in the 18th century along the Boston Post Road, with businesses catering to travelers.

One such establishment, the Golden Ball Tavern, has been preserved as a museum, while the Josiah Smith Tavern was in the process of being converted into a restaurant at the time of this writing.

Weston is situated along both the Bay Circuit Trail, which encircles Boston’s outer suburbs, and a segment of the Mass Central Rail Trail, continuing into Wayland adjacent to it.

In Weston’s countryside, visitors can engage in cross-country skiing at the Weston Ski Track, explore an educational farm, ascend the picturesque slopes of a former ski resort, and traverse the unspoiled vistas surrounding the Weston Reservoir.

1. Golden Ball Tavern Museum

Situated on the Boston Post Road, near Weston’s center, this Georgian tavern was constructed in 1768 and remained within the same family for the subsequent two centuries.

The most notable period at the Golden Ball Tavern occurred during its first decade, as the tavern keeper Captain Isaac Jones was initially a Loyalist, ultimately supporting the Revolutionary cause when the conflict erupted.

Prior to this shift, he would host British soldiers conducting reconnaissance around Weston, leading to the tavern being raided by local Patriots following the Boston Tea Party in 1773.

The building was restored in the 1970s and features rich collections, much of which originated from the Jones family. You can partake in free Second Sunday Open House Tours to explore the preserved interiors and learn more about the tavern’s 18th-century history.

2. Spellman Museum

Weston is home to Regis College, a private Roman Catholic university established in 1927, which enrolled up to 2,000 students at the time of this writing.

In the late 1950s, Archbishop of New York, Francis Spellman (1889-1967), donated his remarkable collection of stamps and other philatelic memorabilia to the museum, leading to its opening to the public in 1960.

The museum’s vast holdings have expanded since then, with collections amassed by notable figures such as Dwight D. Eisenhower, General Matthew Ridgeway, and musician Jascha Heifetz.

The display cases showcase stamps from around the world, dating back to the 19th century, complemented by exhibits that document the history of mail as a means of communication and connection.

3. Cat Rock Park

This beloved town-owned area encompasses 130 acres of woodlands, fields, and wetlands, featuring one of the highest elevations in the town.

Cat Rock Hill was formerly the site of a ski area active from the 1950s to the 1970s and is thought to be named after the bobcats, which were once prevalent in the vicinity.

The summit is located at the southwestern corner of the park, while further north lies an 80-acre field that transitioned from agricultural land to hunting grounds for deer and quail in the 1950s.

This area is adjacent to the picturesque Hobbs Pond, which was dammed in the 1950s for trout fishing. Featuring 5.5 miles of trails, Cat Rock Park is a favored off-leash area for dog owners.

4. Town Green District

The oval green space at the intersection of the Boston Post Road, School Street, and Church Street has served as the civic and religious heart of Weston for over 300 years. It is also where the town’s iconic sights can be observed.

The standout structure is the distinctive First Parish, constructed from fieldstone in a Gothic Revival style in 1888, with a historical lineage tracing back to the late 17th century.

Nearby, adjacent to the elegant old public library building (1899), stands the Josiah Smith Tavern, a significant stagecoach stop along the Boston Post Road for nearly a century after its construction in 1757.

5. Rose Art Museum

Located just across I-95 from Weston, Brandeis University warrants a visit primarily for its outstanding art museum.

Founded in 1961, the Rose Art Museum boasts one of the largest collections of contemporary and modern art in the region, encompassing over 9,000 pieces.

This remarkable collection includes works by renowned artists such as Picasso, Warhol, Mona Hatoum, Yayoi Kusama, Gauguin, Matisse, and Roy Lichtenstein, among numerous others.

The museum is equally noted for its significant temporary exhibitions, and at the time this list was compiled, it featured exhibitions for Peter Sacks and Frida Kahlo, alongside permanent installations by Chris Burden (outside) and Mark Dion.

6. Mass Central Rail Trail

A comprehensive trail initiative is developing between Northampton and Boston, transforming the former railbed of the Massachusetts Central Railroad into a multi-use path that spans over 100 miles.

As of the time of writing, the Mass Central Railroad comprised several disconnected sections, one of which extends through Weston entirely and is paved.

This trail runs roughly parallel to the Boston Post Road, passing to the north of Weston’s Town Green and is soon expected to contribute to a continuous 25-mile segment from Berlin to Waltham.

To access the trail, there are parking facilities at Church Street, Town House Road, and Concord Road, allowing for travel westward to Wayland center or a diversion into Weston’s beautiful Jericho Town Forest.

7. Bay Circuit Trail

Weston is situated along a 230-mile trail that skirts Greater Boston, incorporating a combination of conservation lands, public parks, and tranquil rural roads.

Moreover, the town is located at an intriguing section of the trail that temporarily bifurcates into two segments, one through Sudbury to the west and the other through Weston to the east.

While hiking the trail in Weston, visitors will traverse the charming Jericho Town Forest, which spans 550 acres of woodlands, open fields, and wetlands.

Further north lies Ogilvie Town Forest, an area where wetlands and vernal pools are interspersed with notable bedrock ledges. From there, adventurers will enter Mass Audubon’s Drumlin Farm, home to one of the highest elevations in Greater Boston.

8. Weston Friendly Society of the Performing Arts

Weston claims the distinction of hosting the second-oldest community theater in the nation, established in 1885.

Originally, this venue served as a platform for group readings of poetry, classic literature, and biblical passages for members of the First Parish Unitarian Church.

Over time, the society has transformed into an inclusive theater group, presenting a season of cabaret-style performances in the stately old auditorium at Weston Town Hall, built in the Georgian Revival style in 1917.

Selections from recent seasons have included A Chorus Line, The 25th Annual Putnam County Spelling Bee, Beauty and the Beast, Annie, and Sweet Charity.

9. Weston Reservoir

For a serene hiking experience in Weston, visitors can venture along the shores of this reservoir, constructed at the beginning of the 20th century as part of an advanced water supply system for Boston.

Since the 1960s, Weston Reservoir has functioned as a backup distribution reservoir and is still under the care of the Massachusetts Water Resources Authority.

Being that this is MWRA land, certain activities are restricted; however, the west side at Ash St presents a beautiful setting for hiking amid the surrounding coniferous forests.

Following the southern shore is the Weston Aqueduct trail, which aligns with the route of the grass-covered underground aqueduct that has connected this reservoir to the Sudbury Reservoir in Framingham since its establishment in 1903.

10. Weston Ski Track

Founded in 1974, this cross-country skiing facility located in the southeast part of the town is overseen by the Massachusetts Department of Conservation and Recreation (DCR).

The Weston Ski Track features snowmaking capabilities along its illuminated 2.5 km ski area, in addition to another 13 km of groomed trails reliant on natural snowfall.

Equipment rentals, along with group and private lessons, are offered throughout the season, which typically extends from mid-December to mid-March. During warmer months, the Weston Ski Track transforms into the public Leo J. Martin Golf Course, one of two state-owned golf courses in Massachusetts.

11. Land’s Sake Farm

The Case family first settled in Weston in 1863 and established an extensive estate near the town center.

Beginning with Marion Case in the early 20th century, this land has a history of experimental agricultural practices and was the site of the nursery for Harvard’s Arnold Arboretum from the 1940s until recently.

The Case family mansion has now been converted into offices for the local public school district. In 1985, the town acquired 40 acres from Harvard to create a functioning town farm aimed at providing educational programming for both children and adults.

Casual visitors can stop by the farmstand, offering a variety of organic produce harvested on-site, as well as local goods including honey, maple syrup, and handmade crafts.

12. Norumbega Tower

Eben Norton Horsford (1818-1893), a Harvard scientist remembered for his development of double-acting baking powder, was also intrigued by the possibility of Viking settlements in New England, despite the lack of archaeological evidence.

He speculated that the Eastern Algonquian word Norumbega—generally interpreted as referring to the coastal New England region—derived from Norvega, meaning Norway.

In 1889, believing he had discovered the site of a Norse fort and city, he constructed a 38-foot fieldstone tower, complete with a spiral staircase leading to the top.

The view overlooking the Charles River to the east is most striking in winter when surrounding trees are stripped bare.

13. Weston Art & Innovation Center

Also located on the town green is the building that once served as the town’s public library. Constructed in 1899, this Romanesque Revival edifice housed the library until 1996, when operations were moved to a more modern facility.

Since that time, the former library has functioned as temporary town offices, recreation offices, and for various recreational programs, before ultimately reopening as the Weston Art & Innovation Center in 2021.

As a branch of the public library, the center operates as a studio and maker space, hosting numerous cultural events and providing classes in a diverse range of skills, from fine arts to culinary arts, floral design, pottery, and textiles.

14. Weston Public Library (WPL)

The town’s public library was established in 1857, previously operating in a room within Weston’s old town hall before transitioning to the Old Library building.

Today, WPL is noteworthy for maintaining one of the highest per-capita circulation rates among libraries in the state, with approximately 6,700 items checked out weekly.

The library serves as a vital community resource for various reasons, largely due to the initiatives of the Friends of the Weston Public Library.

This organization provides funding for the library’s History Room, facilitates exhibitions featuring local artists, and organizes regular live performances in the Community Room.

15. Drumlin Farm Wildlife Sanctuary

Situated nearby in Lincoln, the headquarters of the Massachusetts Audubon Society is a sanctuary established in the 1950s, where Drumlin Farm merges a working farm with extensive woodlands intersected by the Bay Circuit Trail.

Children will delight in observing the farmyard animals, including goats, cows, chickens, sheep, and pigs, while also learning about sustainable farming practices and procuring seasonal produce at the farm stand.

The sanctuary offers four miles of trails that meander into its wilder areas, leading visitors to the crest of the glacial drumlin, one of the highest points in Greater Boston.