15 Best Things to Do in Brookline (MA)

Written by Jan Meeuwesen
Updated on
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The birthplace of John F. Kennedy, Brookline is a town directly west of Boston, with lush parkland, two National Historic Sites and colorful neighborhoods to visit.

JFK’s birthplace and childhood home is a National Historic Site, especially remarkable for the work of his mother Rose Kennedy in returning the building to how it looked in 1917.

Brookline is noted for its Jewish community, which comes to the fore at vibrant Coolidge Corner, where there’s a clutch of Kosher bakeries and delicatessens, to go with diverse dining and shopping.

In 1884 the most important figure in American landscape design, Frederick Law Olmsted (1822-1903), relocated to Brookline.

His home and office are also preserved as a National Historic Site, while his work is visible at a host of public spaces, like Beacon Street, the Emerald Necklace linear parks and Brookline Reservoir Park.

1. John F. Kennedy National Historic Site

John F. Kennedy National Historic SiteSource: Wangkun Jia / shutterstock
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 very house, at 83 Beals Street in Brookline.

The Kennedy family donated the house to the National Park Service in 1967, and JFK’s mother Rose Kennedy (1890-1995) played a central role in restoring the building to its 1917 appearance. This included sourcing all of the furnishings, about a fifth of which belonged to the Kennedy family.

The free 30-minutes tour, From Beals Street to the White House, paints a picture of JFK’s as a child, showing the room in which he was born, his favorite books and the other thing that molded his early years.

The National Historic Site is also the starting point for other tours, like “The Enduring Qualities: the Origins of the Kennedy Family in Boston”, which investigates the origins of the Kennedy and Fitzgerald (maternal) families around Boston’s North End.

2. Larz Anderson Auto Museum

Larz Anderson Auto MuseumSource: Keith J Finks / shutterstock
Larz Anderson Auto Museum

In 1899 the historic Weld estate was purchased from a family member by the socialite Isabel Weld Perkins (1876-1948),who moved here with her husband, diplomat Larz Anderson (1866-1937).

The estate’s mansion was pulled down after WWII, but a surviving element is the Châteauesque carriage house (1888), which became a repository for the couple’s extensive collection of early automobiles.

This is now an auto museum, with what is billed as “America’s Oldest Car Collection”, offering an opportunity to get close to early cars that are normally hidden away in private collections.

A few notables are the Winton Phaeton that the couple purchased in 1899, a 1903 Gardner-Serpollet, a 1900 Rocket-Schneider, an extremely rare 1905 Electromobile and a 1910 Panhard et Levassor.

The museum stages a variety of shows for European and American cars on the lawn in summer.

3. Coolidge Corner

Coolidge CornerSource: Wangkun Jia / shutterstock
Coolidge Corner

Brookline’s largest and busiest commercial district is at the intersection of Harvard and Beacon streets, and is the kind of downtown area that most towns aspire to.

Coolidge Corner is bustling, attractive and has an interesting food scene, with the densest collection of kosher restaurants in the Boston area.

The mainstay is Zaftigs Delicatessen, for matzo ball soup, latkes, lox, pastrami and the like. The Olmsted-designed Beacon Street is part of Coolidge Corner’s charm, with a stately, tree-lined boulevard sandwiching the C Branch for swift transport links between Brookline and Boston.

For a bit of shopping there’s a surfeit of independent stores here. One local star is the much-loved Brookline Booksmith, dating back to 1961 and with a progressive attitude and an exciting schedule of readings, conversations with authors, children’s events and more.

4. Frederick Law Olmsted National Historic Site

Frederick Law Olmsted National Historic SiteSource: Wangkun Jia / shutterstock
Frederick Law Olmsted National Historic Site

In Brookline you can visit Fairsted, the home and office compound for the world’s first full-sized professional firm for landscape design.

Frederick Law Olmsted relocated to Brookline in 1883 to be closer to his frequent collaborator, architect H. H. Richardson (1838-1886), who was based close by.

Fairsted was adapted from a Federal farmhouse and barn from the early 19th century, and used by the Olmsted firm for decades until finally being acquired by the National Park Service in 1980.

A ranger-guided tour takes in the Historic Design Office for an insight into the work of Olmsted and his sons, while the encompassing landscape has been designed to reflect Olmsted’s theories.

5. Coolidge Corner Theater

Coolidge Corner TheaterSource: madprime / Flickr | CC BY-SA
Coolidge Corner Theater

Integral to Coolidge Corner’s charm is this fine Art Deco cinema, which opened in 1933 and was actually converted from a Universalist church built in 1906.

With four screens, including the plush main auditorium, this is a place to catch new Hollywood releases, but also classic movies and independent and foreign films.

Like all downtown cinemas, the Coolidge Corner Theater experienced tough times with the rise of video in the 1980s, but in 1989 was purchased by a local real estate magnate who leased it to the Coolidge Corner Theatre Foundation for 99 years.

Some interesting personalities connected to this place are actor Julianne Moore, who was a regular when she was studying at Boston University in the early 1980s, and comedian and Brookline local John Hodgman, who worked here as a teenager.

6. Emerald Necklace

Emerald NecklaceSource: Adam Gladstone / shutterstock
Emerald Necklace

Running along Brookline’s eastern boundary is a chain of interconnected parks and pathways drawn up by Frederick Law Olmsted between 1878 and 1895.

This innovative and trailblazing system adds up to more than 1,100 acres, or seven miles of trails. The Emerald Necklace is mostly threaded by the Muddy River, which was transformed from a series of brackish swamps into a chain of winding brooks and tranquil ponds.

Starting with the Riverway at Brookline’s northeastern tip, you can travel south or east on foot or by bike through a beautiful green, landscaped corridor. This will take you as far as Franklin Park in the south, or east to Boston Common.

7. Larz Anderson Park

Larz Anderson ParkSource: Keith J Finks / shutterstock
Larz Anderson Park

The 64-acre park surrounding the Larz Anderson Auto Museum deserves some time for its sumptuous landscaping, views of Boston and winter attractions.

The park’s location, within minutes of Jamaica Pond at the south end of the Emerald Necklace, means that it is often considered an extension of that string of green spaces.

Larz Anderson Park is the largest public park in Brookline, and the crest of the ridge where the grand mansion once stood affords sensational views of the Boston skyline, particularly pretty at sunset.

There’s an outdoor skating rink at the summit, open December through February, and the hilly landscape provides some of the best sledding in the Boston area.

In the warmer months, the pond is a big draw, along with picnic tables with BBQ grills, a tree-shaded playground and baseball/softball fields.

8. Puppet Showplace Theater

Puppet Showplace TheaterSource: Michael Arena / Wikimedia | CC BY-SA 4.0
Puppet Showplace Theater

Dubbed New England’s favorite puppetry destination, the Puppet Showplace Theater has been running half a century now, and moved to its current location in Brookline Village in 1982.

The theater is managed by a non-profit organization, and stages 300 performances every year. There are family shows for kids, as well as a slew of youth workshops, while the theater also appeals to older audiences with “Puppets at Night” shows and the annual Puppet Slam Camp.

Puppet Showplace Theater was established by Boston teacher Mary Churchill (1930-1997), who found puppets effective for children having trouble learning to read, and later started creating her own shows.

The organization made headlines during the 1980s when several shows by artist in residence Paul Vincent Davis earned Citations of Excellence from UNIMA-USA.

9. Brookline Farmers’ Market

Farmers MarketSource: Matej Kastelic / shutterstock
Farmers Market

Another great thing about Coolidge Corner is the farmers’ market, held at the Centre Street West Parking Lot from the first Thursday in June to the last Thursday before Thanksgiving.

The Brookline Farmers’ Market has been running since the 1970s, and almost everything sold here has been produced in the Commonwealth of Massachusetts.

The selection changes by the week, but normally includes local fruit and vegetables, meats, fish, cheeses, herbs, dairy goods, flowers, fresh roasted coffee, fermented foods, sauces, gourmet ice cream, fresh breads and a lot of fancy sweet treats.

10. Allandale Farm

TomatoesSource: vaivirga / shutterstock

Proudly connecting Brookline and Boston to their agricultural roots is a working farm, the last to be found in either community. Allandale Farm has a documented history going back to 1655, and its farmhouse is one of the few surviving 18th-century buildings in Brookline.

Using organic growing methods the farm produces lettuce, kale, tomatoes, sweet potatoes, melons, hot peppers and more, all sold at the farmstand along with a wonderful selection of locally produced foods, including pies, cookies, breads and nuts.

There’s also a garden center/greenhouse, open April through October, for perennials, annuals, vegetables, herbs and much more. Allandale Farm has an Outdoor Summer Program for children aged 4-13, offering outdoor fun and a taste of farm life in the city.

11. Brookline Reservoir Park

Brookline Reservoir ParkSource: haboston / shutterstock
Brookline Reservoir Park

A short walk from the Frederick Law Olmsted National Historic Site is a 21-acre reservoir, built in 1848 to supply water to Boston. The Brookline Reservoir was once the terminus for the 14-mile Cochituate Aqueduct, running to this spot from Lake Cochituate in Natick.

There’s a beautiful ribbon of landscaped and newly renovated greenery edging the water, with willows, cherry trees, benches and a track for walking and jogging.

Meeting you at the northeast corner is the Principal Gatehouse, built from granite, with a pediment, quoins and window arches in a lighter tone.

This is all framed by Boylston St (Route 9) to the north, as well as rows of grand residences to the east, west and south. If there’s a perfect time to come it’s when the cherry trees are in bloom, around late April or early May.

12. Edward Devotion House

Edward Devotion HouseSource: oliva732000 / Flickr | CC BY-SA
Edward Devotion House

One of the oldest colonial residences in Brookline is maintained by the Brookline Historical Society. The Devotion family had been prominent in local affairs since the mid-17th century, and petitioned for the town’s separation from Boston at the turn of the 18th century.

One, Edward Devotion left a bequest for public schooling in 1744—this wasn’t taken up until the late 19th century when the town purchased the Edward Devotion House and its surrounding land.

The current house was thought to have been built in the mid-18th century, but has many details such as wood framing going back at least 60 years before. For an inside look, you can tour the Edward Devotion House on the first and third Sundays of the month, June through October.

The interior is filled with 18th and 19th-century furnishings, and there’s a large collection of objects relating to the Devotions, as well as other prominent local families like the Goddards.

13. St. Aidan’s Church

St. Aidan’s Church EntranceSource: chris.rycroft / Flickr | CC BY
St. Aidan’s Church Entrance

Something to see from the outside is the former church where John F. Kennedy and Robert F. Kennedy were baptized.

The Tudor-style building was constructed in 1911, while the nearby rectory was built for an earlier church and dates to c. 1850-1855.

St. Aidan’s Church was placed on the National Register of Historic Places in 1985, and was closed in 1999 when it was converted into mixed income housing.

This had been the Kennedy family’s local place of worship when they were living on Beals Street, and John F. Kennedy was baptized here in 1917. There’s a plaque along Freeman St. noting the history of this site.

14. Longyear Museum

Longyear MuseumSource: Longyear Museum / Facebook
Longyear Museum

The founder of the Church of Christ, Scientist, Mary Baker Eddy (1821-1910) is a fascinating figure, whose written works have made a profound impression on millions of people.

Mrs. Eddy was particularly active in the Boston area, and in 1935, after a bequest by philanthropist Mary Beecher Longyear (1835-1931), a museum was established documenting Eddy’s life and the early story of the Christian Science religion.

This has preserved several of Eddy’s residences, while the main gallery opened to the public at a new location in Chestnut Hill in 2001.

The permanent exhibits study the major events in Eddy’s spiritual life, details about the Baker family’s Christian roots, and display artifacts from Pleasant View (NH), where Eddy saw important milestones in the Christian Science movement.

15. Armory Playground and Hall’s Pond Sanctuary

Armory Playground and Hall’s Pond SanctuarySource: chris.rycroft / Flickr | CC BY
Armory Playground and Hall’s Pond Sanctuary

In the north of the town, near the Boston University campus, is a set of adjoining public spaces for active and passive recreation.

At the heart of all this is the Armory Playground, where mature oaks sit on the margins of sports facilities for baseball/softball and tennis (six clay courts).

To the east is the idyllic Hall’s Pond Sanctuary, with preserved woods and a delightful formal garden on the banks of a natural pond.

You can take a stroll at this oasis for a relaxing few minutes, spotting a surprising amount of wildlife, including herons, woodpeckers, turtles and sometimes even owls.


15 Best Things to Do in Brookline (MA):

  • John F. Kennedy National Historic Site
  • Larz Anderson Auto Museum
  • Coolidge Corner
  • Frederick Law Olmsted National Historic Site
  • Coolidge Corner Theater
  • Emerald Necklace
  • Larz Anderson Park
  • Puppet Showplace Theater
  • Brookline Farmers’ Market
  • Allandale Farm
  • Brookline Reservoir Park
  • Edward Devotion House
  • St. Aidan’s Church
  • Longyear Museum
  • Armory Playground and Hall’s Pond Sanctuary