Blake Walsh

15 Best Things to Do in Brookline, MA

  • Published 2023/07/30

Brookline, Massachusetts is an enchanting and serene town situated gracefully between the counties of Suffolk and Middlesex.

It boasts a scenic location that is bordered by Boston, lending it easy accessibility to one of America’s most vibrant cities.

Originally known as Muddy River, the area was settled in 1638 and incorporated as a town in 1705.

With a population of over 60,000, Brookline is a flourishing and diverse neighborhood that draws both locals and tourists to its many parks and vibrant cultural and culinary scene.

While the town boasts many attractions and activities for visitors to enjoy, the most notable is its historical significance as the birthplace of President John F. Kennedy

Whether you’re looking for top-rated restaurants, boutique shopping, or outdoor recreations, Brookline has something for everyone.

If you’re planning to visit the Boston area, make sure to try the 15 best things to do in Brookline, Massachusetts.

How this article was written: Our team first analyzed the scores and feedback across major platforms like Google Maps, Yelp, and Trip Advisor, considering not only the ratings but also the consistency of positive feedback. Following this, we conducted interviews with over 30 local residents who have been to these attractions and places to gather authentic, first-hand experiences. You can read more about our research process here.

While this list showcases some remarkable attractions, it’s important to note there are many other exceptional places in Brookline that are not featured here. Our aim is not just to guide you to popular places but to encourage you to venture out and experience the city for yourself.

Explore the Legacy of Landscape Design in Frederick Law Olmsted National Historic Site

Exterior of Frederick Law Olmsted National Historic Site

Wangkun Jia /

Frederick Law Olmsted National Historic Site combines landscape architecture, American history, and preservation all in one place.

This historic site is easily located on Warren Street and you can access it by public transportation.

Be ready to discover the wonders of landscape architecture as you explore the country’s first professional landscape architecture office.

Take a tour around the grounds of this wonderful location, visit the main house, the office, and the surrounding gardens and grounds.

Interior of Frederick Law Olmsted National Historic Site

Wangkun Jia /

Its grounds are meticulously maintained and feature some of Olmsted’s signature design elements, like winding paths and naturalistic plantings.

You can even bring a scrumptious picnic lunch, laden with your favorite delicacies, and relish the breathtakingly beautiful scenery around you.

Don’t miss out this opportunity to see Olmsted’s legacy and his contributions to shaping the American landscape.

Unwind and Reconnect with Nature in Corey Hill Park

Are you looking for a scenic and fun outdoor destination? Look no further than Corey Hill Park!

Named after Timothy Corey, this picturesque park is a must-visit spot for anyone who loves nature and outdoor activities.

It boasts a stunning view of the Boston skyline, which makes Corey Hill Outlook a highlight of the park.

Imagine picnicking with your loved ones while taking in the breathtaking views around the park; it’s an experience you won’t soon forget.

For families with children, the park’s large playground is a wonderland.

Kids of all ages will love playing on the swings, slides, and climbing structures, while parents can relax on nearby benches and picnic tables.

And with plenty of wildlife to spot, including squirrels, chipmunks, and birds, you’re sure to have an unforgettable outdoor adventure.

Grab your family and friends and head over to Corey Hill Park today for a day of fun, adventure, and unforgettable memories!

Pick Your Own Fresh Produce in Allandale Farm

Allandale Farm, located at 259 Allandale Road, is a historic and beloved farm that has been providing fresh produce and a sense of community to the Boston area.

The farm is home to a wide range of crops, from sweet corn and tomatoes to cucumbers and pumpkins.

Visitors to the farm can explore the fields, pick their own produce, and learn about sustainable agriculture and farming practices.

Roam around and you’ll find the greenhouse that shelters a variety of flowering plants, herbs, vegetables, and more in their greenhouse.

But Allandale Farm is more than just a source of fresh food — it is also a community gathering place, with events and programs throughout the year.

You can spend your birthdays, weddings, business lunches, family reunions, and so much more in some scenic locations around the farm.

Your kids will have lots of fun with the Outdoor Summer Program that offers outdoor activities and learning opportunities for kids aged 4-13 years old.

Come and visit Allandale Farm and experience the beauty of local farming for yourself!

Discover Automotive History at the Larz Anderson Auto Museum

Exterior of Larz Anderson Auto Museum

Yingna Cai /

Do you want to see some of the most amazing cars in the world? Then, Larz Anderson Auto Museum is the place for you.

Housed inside the original Anderson Carriage House on 15 Newton Street, this museum is like no other — it’s filled with unique cars from different ages.

Larz Anderson Auto Museum showcases a diverse collection of automobiles purchased by Larz and Isabel Anderson.

You can find a couple of exhibits in the museum including “The Anderson Collection” which is known as “America’s Oldest Car Collection”.

Ferrari at Larz Anderson Auto Museum

ColinMB, CC BY-SA 3.0, via Wikimedia Commons

In addition to the exhibits in the museum, there are also educational forums, lawn events, and an archive of automotive material kept in the Joseph S. Freeman Research Library.

After having a good look at the exhibits inside the museum, take yourself out for a walk and visit the grounds of Larz Anderson Auto Museum that features acres of open space with walking paths all throughout, a pond, and an ice skating rink that is open to the public during winter season.

The Larz Anderson Auto Museum is truly a must-visit for anyone interested in cars and the history of the automobile and also the curious ones.

Meet Local Farmers in Brookline Farmers Market

Situated on Centre Street West Parking Lot, the Brookline Farmers Market is a local treasure that you wouldn’t want to miss.

Every Thursday, the market comes alive with the sights and smells of fresh, locally grown produce, artisanal products, and delicious foods.

For over forty years, the farmers’ market has been providing fresh fruits, vegetables, baked goods, sweet treats, and more.

By shopping locally, you’re not only getting the freshest food possible, but also supporting small, independent businesses and farmers in the area.

Plus, you’ll have the opportunity to chat with the growers and producers and get some tips on how to grow your own.

So, make sure to include Brookline Farmers Market on your weekly grocery run and enjoy the best of what the local food scene has to offer.

Step into the World of JFK with a Tour of the John F. Kennedy National Historic Site

Signage of John F. Kennedy National Historic Site

Pi.1415926535, CC BY-SA 3.0, via Wikimedia Commons

Located at 83 Beals Street, you will find the exact replica of what was once the residence of America’s president, John F. Kennedy.

John F. Kennedy National Historic Site is a historic place that you can visit where you can have a glimpse of the life and legacy of President Kennedy.

This historic site is the birthplace of one of America’s most beloved presidents and is full of interesting tidbits about the Kennedy family.

You can join a guided tour around the neighborhood, which begins at his birthplace on to his second home where the family moved in 1920.

As you march your way down the street, you’ll learn more about the early years of the President, his family, childhood, family expectations, and so much more.

The original furnishings are also displayed inside the house to give it an authentic feel, as if you were visiting his actual birthplace.

It is an experience that will give you a deeper understanding of the life and legacy of John F. Kennedy.

Have a Puppet-Tastic Day at the Puppet Showplace Theater

Looking for a fun and quirky way to spend an evening around the town? Look no further than the Puppet Showplace Theater.

The Puppet Showplace Theater is a true gem of entertainment that will make you feel like a kid again.

With a line-up of talented puppeteers, this place is guaranteed to put on a show that will leave you wanting more.

From traditional hand puppets to shadow puppets and marionettes, there’s something for everyone to enjoy.

And if you’re feeling creative yourself, be sure to check out the theater’s workshops and classes, where you can learn how to make your own puppets come to life.

So take a break from the hustle and bustle of life and let the Puppet Showplace Theater whisk away your stresses in life and have a puppet-tastic time!

Experience the Vibrant Culture and Cuisine of Coolidge Corner

Daytime view of Coolidge Corner

Wangkun Jia /

Coolidge Corner is the place where history and modernity come together like peanut butter and jelly.

This neighborhood is like a little oasis of joy just a short distance from the bustling city of Boston.

For over 150 years, Coolidge Corner has been continuously attracting visitors and locals alike with its many establishments that offer different kinds of fun.

Coolidge Corner takes its name from the family that operated a general store in the mid-1800s and served wealthy Boston residents.

Shops at Coolidge Corner

Yingna Cai /

Today, this bustling neighborhood is a local attraction and a business hub filled with small shops and restaurants.

Coolidge Corner is very easy to spot — its distinctive clock tower on S.S Pierce Building is the landmark that you should watch out for when you’re riding the trolley up to Beacon Street.

Whether you’re a local looking for a weekend getaway or a tourist exploring the Boston area, be sure to put Coolidge Corner on your list of must-see destinations.

Explore Jewish Art and Culture Kolbo Fine Judaica Gallery

The Kolbo Fine Judaica Gallery on 437 Harvard Street is a unique shopping experience that offers a wide selection of quality Judaica items.

Having opened its doors in 1978 as a specialty store dedicated exclusively to Judaic arts and crafts, Kolbo Fine Judaica Gallery has been an integral part of Brookline’s Jewish community since its founding.

From traditional items like tallit, tefillin, and mezuzah to modern items like fashion jewelry and home décor, Kolbo has something for everyone.

Since then, the gallery has evolved to become the go-to spot for anyone looking for quality Judaica items.

With its wide selection of quality Judaica items, knowledgeable staff, and inviting atmosphere, a visit to Kolbo is sure to be enjoyable and educational.

Unleash Your Creativity in the Clayroom

The Clayroom is the perfect place where you can explore your creative side and get your hands dirty with clay, paint, and much more.

Whether you’re a first-time potter or a seasoned professional, you’ll find something to suit your needs.

At The Clayroom, you can take classes to learn the basics of pottery and clay sculpting, or you can purchase your own supplies and work on your own.

From pottery and wheel-throwing classes to mosaics and sculpture, you’ll discover something new each time you visit.

They also offer kids classes, adult classes, and even private classes for those who want to get a more in-depth experience.

With its welcoming and encouraging atmosphere, you’ll be sure to have a great time and come away with something special that you’ve made with your own two hands!

Come and visit The Clayroom at 1408 Beacon Street and have a great time creating unique pieces of art and learning new techniques.

Admire the Beauty of Emerald Necklace

Trail at Emerald Necklace

Robert Linsdell from St. Andrews, Canada, CC BY 2.0, via Wikimedia Commons

Brookline, Massachusetts is home to one of the most beautiful parks in the country – the Emerald Necklace.

Designed by the famous landscape architect Frederick Law Olmsted, this park system is a true gem that deserves to be explored by locals and visitors alike.

The Emerald Necklace is made up of five parks that are connected by a series of trails and waterways.

Starting from the Boston Common, it stretches for 7 miles through Brookline, and is a perfect place to escape the hustle and bustle of the city.

Whether you want to go for a jog, take a bike ride, or simply go for a walk, there’s a trail or path for you to explore.

With its beautiful parks, stunning views, and rich history, it’s no wonder that it’s a favorite among locals and visitors alike.

So pack a picnic, grab your camera, and come and experience the beauty of the Emerald Necklace for yourself.

Discover the Joy of Playing in Jean B. Waldstein Playground

Jean B. Waldstein Playground in Strathmore Road is a fantastic place to take your kids for a fun day out.

The playground features a wide variety of play structures and activities for children of all ages.

Jean B. Waldstein Playground features splash pads, basketball courts, baseball and softball fields, athletic fields, tennis courts and baseball fields for the sporty ones.

There are also plenty of benches and picnic tables, so you can relax while the kids play.

You can even bring your furry friends for a fun time in the Green Dog Park!

The park has plenty of green space, perfect for a picnic or just to sit and relax and take in the sunshine.

So, if you’re in the Brookline area, be sure to check out Jean B. Waldstein Playground.

Enjoy Nature’s Beauty in Larz Anderson Park

Lush greenery at Larz Anderson Park

Yingna Cai /

The Larz Anderson Park is a piece of oasis nestled in Goddard Avenue and Newton Street that you should stop by while you’re in town.

This 64-acre park offers more than just strolling, it’s a destination that offers a wide range of activities for everyone.

The park boasts a lovely pond, perfect for a romantic picnic with your special someone or a peaceful reflection on your own.

There’s also a playground for the little ones, equipped with all the essentials for a fun-filled day.

What sets this park apart from the others is that it is home to a car museum where you can find a fascinating collection of antique automobiles that will take you back in time.

The stunning views from the top of the hill is also a highlight of the park, where you can take in the sights of both downtown Boston and the park itself.

Whether you’re looking for a place to relax in the sun, get active with some sports, or learn something new at the car museum, Larz Anderson Park has it all.

Experience Classic Cinema at Coolidge Corner Theater

Welcome to Coolidge Corner Theater—the home of the best indie films, classic films, and new releases.

Since 1933, this historic theater has been a staple in the Brookline community, bringing movie fans together to enjoy films of all kinds.

From the red velvet curtains to the ornate decor, there’s something special about the Coolidge Corner Theater.

But it’s not just the classic charm that makes it so great—it’s the commitment to quality that sets it apart.

The Coolidge Corner Theater prides itself on offering an exceptional movie-watching experience.

Their screenings are always top-notch, plus, their concession stand is full of delicious snacks, from fresh popcorn to ice cream.

There’s nothing quite like the atmosphere of a cinema—and the Coolidge Corner Theater has it in spades.

Step Back in Time in Edward Devotion House

Exterior of the Edward Devotion House

User:Magicpiano, CC BY-SA 4.0, via Wikimedia Commons

Nestled in 347 Harvard Street, stands the Edward Devotion House, a historic house with lots of stories to tell.

The Edward Devotion House is one of the oldest surviving houses in Brookline and is listed on the National Register of Historic Places due to its historic significance.

Its study brick walls and elegant Georgian-style architecture still turn heads today, making it the ultimate example of timeless beauty.

The Edward Devotion House was once home to a prominent local figure, Edward Devotion.

Today, the Edward Devotion House is a cultural hub that celebrates his legacy while providing access to educational resources, programs, and activities for the local community.

The house is filled with antiques and period furniture from the 18th century, giving visitors a glimpse into the past.

There are also exhibits that tell the story of the Devotion family and their experiences in Brookline.

If you’re looking for a unique and interesting experience in Brookline, then the Edward Devotion House is definitely worth checking out.

Final Thoughts

Brookline, Massachusetts is a wonderful place to call home.

With its rich history, diverse community, thriving culture and warm hospitality, Brookline truly stands out as a gem among New England’s many treasures.

Whether you’re interested in exploring the outdoors, shopping, or learning something new, there is something for everyone here in Brookline.

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