Top 15 Attractions and Activities in Brookline, MA

The birthplace of John F. Kennedy, Brookline is a town located directly west of Boston, characterized by its lush parkland, two National Historic Sites, and vibrant neighborhoods. The home of JFK and his family is a National Historic Site, notably restored by his mother, Rose Kennedy, to reflect its original appearance from 1917. Brookline is recognized for its significant Jewish community, highlighted in the lively Coolidge Corner, which features a variety of kosher bakeries, delicatessens, as well as diverse dining and shopping opportunities.

In 1884, prominent landscape architect Frederick Law Olmsted relocated to Brookline. His residence and office are preserved as a National Historic Site, showcasing his work across numerous public spaces, including Beacon Street, the Emerald Necklace linear parks, and Brookline Reservoir Park.

1. John F. Kennedy National Historic Site

On May 29, 1917, the future 35th President of the United States, John F. Kennedy, was born at this residence located at 83 Beals Street in Brookline. The Kennedy family donated the house to the National Park Service in 1967, with Rose Kennedy spearheading the restoration to its 1917 condition, which included sourcing original furnishings, about a fifth of which were from the Kennedy family.

The complimentary 30-minute tour, titled “From Beals Street to the White House,” provides insights into JFK’s childhood, showcasing his birthplace, favorite books, and other influences from his early years. This National Historic Site also serves as the starting point for additional tours, such as “The Enduring Qualities: the Origins of the Kennedy Family in Boston,” which explores the ancestry of the Kennedy and Fitzgerald families in Boston’s North End.

2. Larz Anderson Auto Museum

In 1899, Isabel Weld Perkins (1876-1948) acquired the historic Weld estate from a family member and moved there with her spouse, diplomat Larz Anderson (1866-1937). Although the estate’s mansion was demolished after World War II, the Châteausque carriage house (1888) remains as a repository for their extensive collection of early automobiles.

Currently, this facility functions as an auto museum, recognized as “America’s Oldest Car Collection,” providing visitors with a rare opportunity to view early automobiles typically housed in private collections. Notable vehicles include the Winton Phaeton, purchased in 1899, a 1903 Gardner-Serpollet, a 1900 Rocket-Schneider, an exceptionally rare 1905 Electromobile, and a 1910 Panhard et Levassor. The museum hosts various shows for European and American cars on the lawn during the summer months.

3. Coolidge Corner

Brookline’s principal commercial district is situated at the intersection of Harvard and Beacon streets, embodying the downtown area many towns aspire to emulate. Coolidge Corner is vibrant, appealing, and boasts a diverse food scene, hosting the highest concentration of kosher restaurants in the Greater Boston area.

Zaftigs Delicatessen is a highlight, featuring traditional offerings such as matzo ball soup, latkes, lox, and pastrami. The Olmsted-designed Beacon Street contributes to Coolidge Corner’s appeal, presenting a stately, tree-lined boulevard that facilitates swift transport links between Brookline and Boston.

For shopping enthusiasts, Coolidge Corner offers a plethora of independent stores. A notable establishment is Brookline Booksmith, which has operated since 1961, renowned for its progressive stance and an engaging schedule of readings, author conversations, children’s events, and more.

4. Frederick Law Olmsted National Historic Site

Visitors to Brookline can explore Fairsted, the residence and office of the first full-sized professional firm dedicated to landscape design. Frederick Law Olmsted moved to Brookline in 1883 to collaborate closely with architect H. H. Richardson (1838-1886), who resided nearby.

Fairsted was adapted from an early 19th-century Federal farmhouse and barn, serving as the operational base for the Olmsted firm for many years until it became part of the National Park Service in 1980.

A ranger-led tour includes a visit to the Historic Design Office, offering insights into the work of Olmsted and his sons, while the surrounding landscape showcases Olmsted’s design principles.

5. Coolidge Corner Theater

A significant aspect of Coolidge Corner’s allure is this exquisite Art Deco cinema, which opened in 1933 and was converted from a Universalist church built in 1906. Featuring four screens, including a luxurious main auditorium, this venue showcases the latest Hollywood releases alongside classic films and independent international cinema.

Like many downtown cinemas, Coolidge Corner Theater faced challenges with the advent of home video in the 1980s. However, in 1989, a local real estate investor acquired it and leased it to the Coolidge Corner Theatre Foundation for a 99-year term. Notably, actor Julianne Moore frequented the theater while studying at Boston University in the early 1980s, alongside comedian John Hodgman, who worked there as a teenager.

6. Emerald Necklace

Along Brookline’s eastern boundary extends a network of interconnected parks and pathways designed by Frederick Law Olmsted between 1878 and 1895. This pioneering system encompasses over 1,100 acres and spans approximately seven miles of trails. The Emerald Necklace largely follows the Muddy River, which underwent transformation from brackish swamps into a series of meandering brooks and serene ponds.

Beginning at the Riverway in Brookline’s northeastern corner, visitors can traverse southward or eastward on foot or by bike through a beautiful, landscaped corridor that leads to either Franklin Park in the south or Boston Common in the east.

7. Larz Anderson Park

The 64-acre park surrounding Larz Anderson Auto Museum offers visitors a chance to appreciate its exquisite landscaping, stunning views of Boston, and seasonal winter activities. Its proximity to Jamaica Pond, at the southern end of the Emerald Necklace, often leads it to be considered an extension of this network of green spaces.

This park is the largest public park in Brookline, and the ridge where the mansion once stood provides breathtaking views of the Boston skyline, especially captivating at sunset. The park features an outdoor skating rink open from December through February, and its hilly terrain is known for excellent sledding opportunities in the Boston area. In the warmer months, the pond attracts visitors for picnicking, while amenities such as tree-shaded playgrounds and baseball/softball fields enhance the experience.

8. Puppet Showplace Theater

Recognized as New England’s premier puppetry venue, Puppet Showplace Theater has been operational for half a century, relocating to its present site in Brookline Village in 1982. Managed by a non-profit organization, it hosts 300 performances annually, encompassing family shows, youth workshops, and special events catering to adult audiences, such as “Puppets at Night” and the annual Puppet Slam Camp.

The theater was founded by Boston educator Mary Churchill (1930-1997), who identified the potential of puppetry to assist children struggling with reading. The organization gained notable recognition in the 1980s when various performances by resident artist Paul Vincent Davis received Citations of Excellence from UNIMA-USA.

9. Brookline Farmers’ Market

Another highlight of Coolidge Corner is the farmers’ market, held at the Centre Street West Parking Lot from the first Thursday in June until the last Thursday before Thanksgiving. The Brookline Farmers’ Market has been operational since the 1970s, with nearly all products sourced from within the Commonwealth of Massachusetts.

The selection varies weekly but typically features local fruits and vegetables, meats, fish, cheeses, herbs, dairy produce, flowers, freshly roasted coffee, fermented foods, sauces, gourmet ice cream, and a multitude of sweet treats.

10. Allandale Farm

Allandale Farm serves as a vital connection between Brookline and Boston and their agricultural heritage, being the last working farm in either community. Its documented history extends back to 1655, and the farmhouse is one of the few remaining 18th-century structures in Brookline. Utilizing organic farming practices, the farm cultivates lettuce, kale, tomatoes, sweet potatoes, melons, hot peppers, and more, all available at the farmstand, along with a delightful array of locally produced products including pies, cookies, breads, and nuts.

The site also features a garden center and greenhouse open from April to October, offering perennials, annuals, vegetables, herbs, and much more. Additionally, Allandale Farm operates an Outdoor Summer Program for children aged 4-13, providing an enjoyable introduction to farm life in the city.

11. Brookline Reservoir Park

Located a short distance from the Frederick Law Olmsted National Historic Site, the Brookline Reservoir spans 21 acres and was constructed in 1848 to supply water to Boston. It served as the culmination of the 14-mile Cochituate Aqueduct, delivering water from Lake Cochituate in Natick.

Surrounding the reservoir is a beautifully landscaped trail featuring willows, cherry trees, benches, and a track ideal for walking and jogging. The Principal Gatehouse, constructed from granite, greets visitors at the northeast corner, showcasing pediment accents, quoins, and window arches.

The park is framed by Boylston St (Route 9) to the north, alongside elegant residences to the east, west, and south. The optimal time to visit is during late April or early May when the cherry trees are in full bloom.

12. Edward Devotion House

Maintained by the Brookline Historical Society, the Edward Devotion House stands as one of the oldest colonial residences in Brookline. The Devotion family has been influential in local governance since the mid-17th century and played a pivotal role in Brookline’s separation from Boston in the early 18th century.

Edward Devotion is notably recognized for bequeathing funds for public schooling in 1744, which materialized when the town acquired the Edward Devotion House and its surrounding land in the late 19th century. The current structure is believed to have been built in the mid-18th century, although many architectural features date back at least 60 years earlier. Guests can tour the Edward Devotion House on the first and third Sundays of the month from June through October.

The interior is adorned with furnishings from the 18th and 19th centuries, along with a comprehensive collection of artifacts related to the Devotion family and other notable local families like the Goddards.

13. St. Aidan’s Church

Noteworthy from an external viewpoint is the former church where John F. Kennedy and Robert F. Kennedy were baptized. Constructed in 1911 in a Tudor style, the adjacent rectory dates back to approximately 1850-1855.

St. Aidan’s Church was added to the National Register of Historic Places in 1985 and was repurposed into mixed-income housing following its closure in 1999. This site served as a place of worship for the Kennedy family during their residency on Beals Street, with John F. Kennedy’s baptism occurring here in 1917. A plaque along Freeman St. commemorates the historical significance of this location.

14. Longyear Museum

The Longyear Museum celebrates the life of Mary Baker Eddy (1821-1910), the founder of the Church of Christ, Scientist, whose writings have profoundly impacted countless individuals. Mrs. Eddy was especially influential in the Boston area, and in 1935, the museum was established as a result of a bequest from philanthropist Mary Beecher Longyear (1835-1931), aiming to document Eddy’s life and the early development of the Christian Science religion.

The museum preserves several of Eddy’s residences, while the main gallery opened at its new Chestnut Hill location in 2001. Permanent exhibits explore key events in Eddy’s spiritual journey, the Baker family’s Christian roots, and artifacts from Pleasant View (NH), representing crucial milestones in the Christian Science movement.

15. Armory Playground and Hall’s Pond Sanctuary

In the northern section of the town, adjacent to the Boston University campus, lies a series of interconnected public spaces designed for both active and passive recreational pursuits. Central to this area is the Armory Playground, featuring mature oak trees enveloping sports facilities for baseball/softball and six clay tennis courts.

To the east, Hall’s Pond Sanctuary offers a serene environment with preserved woodlands and a charming formal garden beside a natural pond. Visitors may enjoy leisurely strolls in this tranquil setting, where a variety of wildlife, including herons, woodpeckers, turtles, and occasionally owls, can be observed.