Nestled just outside the bustling city of Boston, Brookline, Massachusetts, is a charming and diverse suburban town that offers a blend of history, culture, and outdoor activities. From historic sites to beautiful parks and a vibrant culinary scene, Brookline has something for everyone. With proximity to Boston and multiple public transportation options, Brookline is a great option for a day trip. In this article, I’ll share some of the top sites to explore and provide suggestions for things to do in Brookline MA to make the most of your visit.
I grew up in the town of Brookline and several family members live there still. In my opinion it was one of the best places to grow up. Though a big town by most standards, Brookline’s many neighborhoods, parks, and recreational facilities created a feeling of community without the limitations of a small town. And how fun it was to jump on the T (subway) with friends for a day in Boston!
I hope this article will entice you to add a visit to Brookline to your New England travel!
Table of Contents
Top 10 things to do in Brookline MA
- Visit the John F. Kennedy National Historic Site: Explore the birthplace and childhood home of the 35th President of the United States, John F. Kennedy.
- Take a stroll in Coolidge Corner: a vibrant neighborhood with shops, restaurants, and a historic movie theater.
- Visit Larz Anderson Park: a beautiful park with picnic areas, walking trails, a playground.
- Car enthusiasts must-do- explore the vintage car collection at the Larz Anderson Auto Museum.
- Stop in at the Brookline Booksmith: Browse through the extensive collection of books at this independent bookstore.
- Discover the Frederick Law Olmsted National Historic Site: the former residence of the renowned landscape architect Frederick Law Olmsted. Learn about his contributions to urban park design.
- Walk the Brookline Reservoir Park: a very popular promenade loop for residents of Brookline!
- Spend time at the Brookline Farmer’s Market: If you’re in town during the warmer months, visit the local farmer’s market to sample fresh produce, baked goods, and artisanal products.
- Visit the Brookline Historical Society: Learn about the history of Brookline through exhibits and artifacts.
- Enjoy outdoor activities in Olmsted Park: Take a bike ride or a leisurely walk through this scenic park,
- Visit the Puppet Showplace Theater: performances for both children and adults at this unique theater.
- Visit the Metropolitan Waterworks Museum. (The museum is in the village of Chestnut Hill which is comprised of Brookline, Boston, and Newtown, so though technically this museum is in corner of Boston, but for all purposes, it’s in Brookline…)
A Brief Introduction to Brookline
As with most New England towns, Brookline is steeped in history. It began as a tiny farming hamlet of Boston in the 1630s known as Muddy River. Eventually as the community grew it chose to incorporate as a separate town in 1705. When electrified streetcar lines extended into Brookline in the late 1880s, the town rapidly became a favorite of Boston commuters.
FUN FACTS about Brookline
- On the April night in 1775, when Paul Revere made his famous ride to Lexington, another patriot, William Dawes, set off from Boston, through Brookline, on the same mission. Dawes’ ride has been forgotten by most, but Brookline celebrates the ride each year on Patriots Day.
- Brookline has had a LOT of famous residents besides Frederick Law Olmsted and the Kennedy family. Graduates of Brookline High School include: Michael Dukakis and his wife Kitty, Mike Wallace, Conan O’Brien, Alan Rachins, Marita Bonner, Robert Kraft, and ME! (Barbara Walters went to Brookline elementary schools before her family moved away)
- With a population around 63,000, Brookline is the most populous town in Massachusetts. It is part of Norfolk County and has chosen to continue with town government.
Exploring Brookline: the neighborhoods
Coolidge Corner, situated in the northern part of Brookline (radiating from Beacon Street), is a bustling and trendy neighborhood. Lined with boutique shops, cozy cafes, and cultural hotspots like the Coolidge Corner Theatre, this area attracts residents and visitors alike who appreciate its artsy and lively ambiance. This is a great option for a day visit to Brookline as it’s right on the MBTA Green Line C and is easily walkable to historic sites like the Kennedy birthplace on Beals Street.
Stop in at the Brookline Booksmith if you’re in Coolidge Corner. This independent bookstore is a haven for literary enthusiasts. Browse through the extensive collection of books, ranging from bestsellers to hidden literary gems. Check their schedule for author events and book readings and immerse yourself in the literary culture of Brookline.
Brookline Village, located in central Brookline, is a historic neighborhood that seamlessly blends old-world charm with modern amenities. Its tree-lined streets, historic architecture, and a mix of local businesses create a charming and welcoming environment. Brookline Village is not only a hub for local commerce but also boasts historical landmarks, including the Old Lincoln School and the charming Linden Park. This is also where you’ll find the large and welcoming Brookline Public Library, a favorite haunt of mine when I lived in town.
Cleveland Circle, situated towards the west (end of Beacon Street), is a lively and youthful neighborhood with a mix of parks, recreational facilities, and diverse dining options. Home to Boston College, Cleveland Circle exudes a college-town atmosphere while still maintaining a strong sense of community.
It’s a short walk from Cleveland Circle to both the Metropolitan Waterworks Museum, the Chestnut Hill Reservoir Park, and DCR Reilly Memorial Rink, an outdoor skating rink. Enjoy these destinations before returning to Cleveland Circle for a slice of my favorite pizza at Pino’s.
South Brookline, encompassing areas such as South Brookline Village and the Allandale Farm area, is a residential area that offers a peaceful escape from the urban hustle. With tree-lined streets and a mix of historic and modern homes, this neighborhood creates a welcoming environment for families. The parks and open spaces in South Brookline provide lots of opportunities for outdoor activities and community gatherings.
The Allandale Farm area is renowned for its pastoral beauty and agricultural significance. Allandale Farm itself is one of the oldest working farms in the Boston area, offering not only fresh produce but also a bucolic setting for visitors. The surrounding neighborhoods benefit from the farm’s presence, fostering a close-knit community with a shared appreciation for local agriculture and nature.
Residents of South Brookline enjoy the proximity to nature reserves, including the Allandale Woods and the Arnold Arboretum. These green spaces provide opportunities for hiking, birdwatching, and a connection to the natural beauty that defines this part of Brookline.
Chestnut Hill, is a village that spans three jurisdictions – Brookline, Boston, and Newton. Within Brookline it’s a prominent neighborhood with some lovely open landscapes, upscale residences, and proximity to Boston College.
Chestnut Hill is where you’ll find the historic Longwood Cricket Club, the site of the first Davis Cup tournament and an active tennis club today. If you’re invited to play on the grass courts of Longwood, be sure to pack your tennis whites!
Things to Do in Brookline MA
Historic landmarks, museums and architecture
John F. Kennedy National Historic Site
Brookline holds a special place in American history as the birthplace of President John F. Kennedy. So, for many visitors to Brookline the JFK National Historic Site is the main attraction. Visitors can explore the site, which includes the Kennedy family’s childhood home, beautifully preserved to offer a glimpse into the life of the 35th President of the United States. The site provides a unique opportunity to learn about the Kennedy family’s legacy and their impact on American politics.
Consider booking a guided tour in advance to ensure a spot, as this site is popular among history enthusiasts.
Fun Fact: My mother was a backdoor neighbor to the Kennedy family, often babysitting the children. So, when you visit the President’s home on Beals Street, peak behind to see my family’s home on Stedman Street.
John F. Kennedy National Historic Site, 83 Beals St., Brookline
The Frederick Law Olmsted National Historic Site (Fairsted)
The Olmsted House, also known as Fairsted, is a significant historical site in Brookline. Designed by Frederick Law Olmsted, the renowned landscape architect responsible for designing New York’s Central Park, the grounds of the U.S. Capital, Boston’s Emerald Necklace and many other iconic landscapes, Fairsted was his home and office.
Located on a quiet street in Brookline, this site administered by the National Park Service is a must-visit for those interested in landscape architecture and design. It offers guided tours that provide insight into Olmsted’s life, work, and the evolution of his ideas that have had a lasting impact on the field of landscape architecture.
Remember to check the opening hours and availability of these attractions before planning your visit.
Frederick Law Olmsted National Historic Site, 99 Warren Street, Brookline
The Larz Anderson Auto Museum
One of the town’s hidden gems, the Larz Anderson Auto Museum, is a must-visit for automobile enthusiasts. This museum of transportation houses an impressive collection of vintage cars, showcasing classics, sports cars, and other historic vehicles. It’s the oldest collection of cars in the U.S. (Car lovers should also consider a trip to the Cape to see another excellent auto collection at the Heritage Museums in Sandwich, MA.)
The collection is housed in an extraordinary “carriage house” designed by Edmund M. Wheelwright, who also designed the Boston Public Library.
Check the website for special exhibitions and events related to automotive history.
Larz Anderson Auto Museum, 15 Newton St., Brookline
Longyear Museum
The Longyear Museum is dedicated to the life and works of Mary Baker Eddy, the founder of the Christian Science movement. The museum houses a collection of artifacts, documents, and exhibits related to Mary Baker Eddy’s life, writings, and the development of Christian Science.
Longyear Museum, 1125 Boylston Street
Historic homes in Brookline
The Edward Devotion House is one of the oldest surviving colonial structures in Brookline and one of the best preserved. It was built around 1745 and originally served as the residence of Edward Devotion, a local farmer, and deacon of the First Parish in Brookline. It is currently the headquarters of the Brookline Historical Society.
The house is tucked within the grounds of the Florida Ruffin Ridley School at 347 Harvard Street, Brookline. (The school, originally called Edward Devotion School was renamed when Devotion’s history as a slave owner came to light.)
The Dutch House (20 Netherlands Rd.) is a fun drive-by destination. This replica of a Dutch town hall was built as an exhibition hall for the World’s Fair in Chicago (the 1893 World’s Columbian Exposition). It represented the Van Houten Cocoa Company. After the event the building was purchased by the wealthy Captain Charles Brooks Appleton, who had the building dismantled and rebuilt in Brookline.
Things to do outdoors in Brookline MA
Brookline is a very city-like suburb. There may not be as much open land as in other towns, but the green spaces that Brookline has are lovely.
My favorite is Larz Anderson Park. There is a fee to enter the auto museum, but the 64 acres of parkland are free for all to enjoy. The park has extensive trails with stunning views of Boston from the top. Bring a picnic to enjoy, let the kids play in the playground, or in the winter, join the fun with some excellent sledding.
In the southern end of Brookline is Allandale Woods, a natural retreat with extensive trails, lush greenery, and diverse wildlife. It’s a great place for hiking, birdwatching, and connecting with the beauty of nature close to the city.
The Arnold Arboretum, located in Boston but just minutes from Brookline, is a horticultural treasure. Visitors can wander through meticulously curated landscapes, learn about a vast collection of plant species, and enjoy the atmosphere. The Arnold Arboretum was designed by Frederick Law Olmsted and is a National Historic Landmark. It is owned by the City of Boston and managed by Harvard University under a 1,000-year lease. Get there before the lease runs out! Ha!
Walkers and cyclists will love exploring the Emerald Necklace, a series of interconnected parks designed by Frederick Law Olmsted. There are picnic tables throughout the parks for water stops. Our favorite stop on the ‘necklace’ is Olmsted Park right on the Boston line.
The Brookline Golf Course is a public course and considered very good. If you’re a an avid golfer try to wrangle an invitation to the Country Club on Clyde St.
For family fun outdoors there are lots of playgrounds and parks. A local favorite is the Brookline Avenue Playground (575 Brookline Ave) which features accessible pathways, a splash pad, and a large playing field. There are lots of other parks to choose from but we’re looking forward to exploring the Fisher Hill Reservoir Park on our next visit. The newly renovated park looks amazing!
Boston Marathon runs through Brookline
One of our family’s favorite traditions was attending the Boston Marathon. My family was so into the marathon that we started the day driving to Hopkinton for the start, stopped once in Wellesley for ice cream and finished the day in downtown Boston waiting for our favorites to cross the finish line. But here’s the thing – the Boston Marathon route goes right through Brookline! Choose a spot in Cleveland Circle or anyplace else along Beacon Street for a front row view of the iconic race!!
Brookline, Massachusetts, draws visitors with its historical sites, cultural offerings, and natural wonders. From the childhood home of John F. Kennedy to the serene parks designed by Frederick Law Olmsted, this town offers something for everyone.
Whether you’re a history enthusiast, a nature lover, or a food connoisseur, a visit to the Brookline area promises a delightful and fascinating experience. Immerse yourself in the local culture, indulge in culinary delights, and embrace the beauty that awaits in this charming Massachusetts town. It’s one of the best things you can do if you’re in the area.
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Amy Tull
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Amy, a writer on responsible bucket list travel, is your reliable source for insightful travel advice. With a career background in libraries, and a degree in biology and mathematics, Amy's approach to travel is rooted in meticulous research and planning, and her commitment to eco-conscious adventures.
Amy’s dedication to sustainable travel practices, including efficient packing techniques, ensures that every adventure leaves a positive impact on both the environment and the traveler's well-being. Trust Amy to guide you towards meaningful and eco-friendly travel, making the most of your retirement years.
A lifelong New England resident, Amy is also the source for insider tips on travel in the Northeastern U.S.
