Top 15 Activities and Attractions in Wellesley, MA

This affluent suburb of Boston is renowned for its distinguished educational institutions.

The most notable of these is the private women’s liberal arts college, Wellesley College, which boasts an impressive roster of accomplished alumni, including Hilary Clinton.

The Wellesley College campus is among the most picturesque in New England, featuring an art museum with an exceptional collection and significant contemporary art exhibits.

Wellesley’s vibrant downtown area serves as the midpoint of the Boston Marathon, where the students of Wellesley College have traditionally created the Scream Tunnel to encourage runners.

1. Wellesley Square

Accessible via an MBTA station on the Framingham/Worcester Line, Wellesley’s primary commercial district is a thriving center for shopping, dining, and culture, with over 100 local businesses.

Adorned with green spaces such as Hunnewell Park, Central Park, Church Park, and Morton Park, Wellesley Square embodies the ideal walkable downtown, with a continuous array of public events throughout the year.

The shopping experience in Wellesley Square includes boutiques, art galleries, florists, artisanal gift shops, a toy shop, and a bookstore, among others. The dining options are extensive and cater to diverse tastes, ranging from classic pizza to gourmet vegan cuisines.

2. Wellesley College

As one of the premier liberal arts colleges in the United States, Wellesley College serves as the town’s largest employer and is proud to count Hillary Clinton, Madeleine Albright, Diane Sawyer, and Cokie Roberts among its impressive alumni.

Established in 1875, the college’s lush campus is uniquely situated on the northern shore of Lake Waban.

Paths wind through coniferous and deciduous groves and across meadows, featuring elegant brick and stone structures like Tower Court that gracefully rise on the rolling hills.

Visitors are welcomed not only for collegiate tours but also for access to the remarkable Davis Museum and the Wellesley College Botanic Gardens.

3. Davis Museum at Wellesley College

Offering free admission, this exceptional art museum is part of a larger ensemble of arts facilities on campus and is connected to the Jewett Arts Center through an enclosed bridge.

Originally established in the 1880s, the Davis Museum occupies a building designed in 1993 by Pritzker Prize-winning architect Rafael Moneo.

The museum’s extensive collection ranges from ancient artifacts, such as a mosaic unearthed in Antioch, to significant contemporary art showcases. Notable pieces include works by Lavinia Fontana, Paul Cézanne, Andy Warhol, Jackson Pollock, John Singleton Copley, Ammi Phillips, and many others.

Current exhibitions feature solo displays from artists such as Sondra Perry, Alexandria Smith, Daniela Rivera, and Fatimah Tuggar.

4. Brook Path (Fuller Brook Park)

Wellesley’s most frequented public park follows Fuller Brook and its tributary Caroline Brook for over three miles throughout central Wellesley.

Initially created in 1899, the Brook Path was designed to enhance drainage in flood-prone areas while also providing public parkland in the town’s core.

Improvements to the park were made during the Great Depression in the 1930s, including regrading and the installation of the stone bridges that remain today. The Brook Path connects with the Crosstown Trail and the Guernsey Path, forming a vital part of Wellesley’s extensive trail system, facilitating car-free access to numerous locations.

The trail meanders through quiet woods, wetlands, and open fields, while also traversing more developed sections such as the recreation facilities at Hunnewell Fields.

5. Massachusetts Horticultural Society’s Garden at Elm Bank

Located southwest of Wellesley, the 182-acre reservation along a bend in the Charles River, formerly a country estate, is recognized on the National Register of Historic Places.

The focal point of the Elm Bank is the 36-acre Elm Bank Horticulture Center, which houses the Massachusetts Horticultural Society. This area features a variety of stunning gardens, all set against the backdrop of the Colonial Revival manor house built in 1907.

Notably, certain garden spaces, including the Italianate Garden, were designed by Percival Gallagher, part of the renowned Olmsted Brothers firm.

Other attractions include the Daylily Garden that blooms mid-summer, the Alan Peyton Rhododendron Garden, the Shade Garden, the Trial Garden, Weezie’s Garden for Children, the Teaching Herb Garden, and the Historic Daffodil and Native Plant Garden, which has been a spring highlight for over two decades.

6. Wellesley College Botanic Gardens (WCBG)

Available for public enjoyment on the north side of the Wellesley College campus, this botanical garden features more than 1,500 taxa from over 150 distinct plant families.

The origin of the gardens can be traced back to the early 1850s, with the establishment of the H. H. Hunnewell Arboretum, which is named for a local resident known for popularizing rhododendrons in the U.S. during the 19th century.

Later in the century, the charming Alexandra Botanic Garden was created, showcasing specimen trees and shrubs from around the world along the banks of the Silver Thread brook and Paramecium Pond.

Additionally, the newly opened Global Flora Conservatory at the Margaret C. Ferguson Greenhouses (2022) acts as a “showcase of living beauty highlighting plant forms” while serving as a hub for interdisciplinary scientific research and education.

Lastly, nestled below the Whitin Observatory is the Edible Ecosystem Teaching Garden, designed to replicate natural ecosystem functions while providing food and useful materials for humans.

7. Hunnewell Park

Nestled adjacent to Wellesley Square, one of the largest public parks in the town may also be its most picturesque setting.

Hunnewell Park boasts rolling lawns and mature trees, dominated by the beautiful Town Hall (1883), which is listed on the National Register of Historic Places.

This architecturally diverse structure showcases Richardsonian Romanesque, Mannerist gables, and Châteauesque elements within its steeply pitched hipped roof and corner towers.

Hunnewell Park is ideal for passive recreation, offering benches, picnic tables, pathways, and a charming pond, all just a few steps from the shops and eateries surrounding Wellesley Square.

8. Wellesley Symphony Orchestra (WSO)

Wellesley hosts a community orchestra, founded in 1948, which is currently under the direction of Music Director/Conductor Max Hobart, a long-standing member of the Boston Symphony Orchestra.

This orchestra is responsible for various regional programs aimed at promoting composers and contemporary music, nurturing young talent, and fostering an appreciation for classical music.

For over 40 years, the Wellesley Symphony Orchestra has been the orchestra-in-residence at Wellesley Community College, presenting approximately six performances annually from October through May.

9. Elm Bank Reservation

The surrounding estate at Elm Bank Reservation has a rich history spanning approximately 300 years.

The designation originates from the elm trees that were planted along the Charles River’s banks in the mid-18th century.

Beyond the gardens, visitors can explore the reservation’s broad, 2.6-mile looping trail that follows the river’s edge through tranquil woodlands.

This accessible trail is family-friendly and permits dogs, provided they are leashed in this area, though they are not allowed in the gardens.

10. Weston Ski Track

The DCR manages this expansive area for cross-country skiing and snowshoeing located just northeast of Wellesley along the Charles River.

Typically operational from December through March, the Weston Ski Track offers 15 kilometers of naturally groomed trails and a snowmaking area with a guaranteed length of 2.5 kilometers.

LED lighting enables nighttime skiing, and all necessary equipment is available at the ski shop, either for purchase or rental.

This facility serves as a center for numerous competitive Nordic ski programs, in addition to providing both solo and group ski lessons, which are seldom canceled due to snowmaking capabilities.

11. Morses Pond Beach

Located on the western town line, Morses Pond is accessible from Wellesley Square and Wellesley College via the Crosstown Trail along the path of the Cochituate Aqueduct.

As a local destination for various water activities such as boating, fishing, and swimming, the pond spans 100 acres, with an extensive wooded parkland and Wellesley’s most popular public beach situated on the eastern side, complemented by a picnic area and a pavilion featuring barbecue facilities.

Morses Pond Beach provides lifeguards daily during the summer break from school, and access requires a beach pass, with seasonal passes available for non-residents.

12. Babson College

The 350-acre campus of this highly regarded private business school is situated in the eastern portion of Wellesley within the Babson Park area.

Adjacent to Olin College of Engineering and established in 1919, Babson College is characterized by its classic New England college campus layout, featuring elegant Georgian Revival architecture, expansive lawns, towering trees, and several state-of-the-art modern facilities.

Guided self-tours are available via downloadable maps, and the campus hosts a packed calendar of conferences, forums, and various events throughout the year.

Additionally, visitors can enjoy performing arts at the 441-seat proscenium Carling-Sorenson Theater, and the institution sponsors 22 varsity sports teams.

13. Boston Marathon

Each year, on the third Monday of April (Patriot’s Day), thousands of runners traverse through Wellesley along Central Street and Washington Street as part of the Boston Marathon.

Wellesley Square marks the official midpoint of this historic race, which has been held since 1897 and is the oldest annual marathon in the world.

Numerous spectators line the streets to support the participants. For many years, the students of Wellesley College have been responsible for creating the Scream Tunnel, a sound barrier of cheers along a quarter-mile stretch of the race that can be heard from a mile away.

14. Wellesley Wonderful Weekend

The annual kickoff for the summer season in Wellesley is characterized by this festive weekend held a week prior to Memorial Day.

Organized by the Wellesley Celebrations Committee, one of the highlights on Saturday is the traditional Veterans Parade, which has been a staple for over fifty years.

This event features an extensive program running from Thursday to Sunday, including a fun fair at Hunnewell Field, a pet parade, an outdoor movie screening, and a fireworks show on Sunday evening to conclude the festivities.

15. Summer Concert Series

Wellesley Town Hall serves as an excellent venue for free live music performances throughout the summer months.

These concerts typically occur on Wednesday evenings from late June to mid-August and feature tribute bands covering a wide range of musical genres, from jazz classics to classic rock and Motown.

Engaging entertainment is also provided for children, while Friday evenings are reserved for child-friendly outdoor movie screenings; popular selections include Finding Nemo, Sonic the Hedgehog, and A Bug’s Life.