12 Best Things to Do in Brookline to Make the Most of your Trip

• Best for families wanting to teach their kids about American history and history buffs - John F. Kennedy Birthplace
• Best for day of shopping, noshing, and doing cool stuff - Coolidge Corner
• Best for auto and history enthusiasts - Larz Anderson Auto Museum

• Best for cinephiles - Coolidge Corner Theatre
• Best for puppet lovers of all ages, especially young children - Puppet Showplace Theater

• Best for four-season family fun - Larz Anderson Park
• Best for runners and joggers - Brookline Reservoir Park
• Best for people who love plants and nature - Allandale Farm

• Best for late date night - Coolidge Corner Theatre After Midnite
• Best for bookworms - Brookline Booksmith

• Best for getting produce for the night's meal - Brookline Farmer’s Market
• Best for lovers of landscape architecture and history - Frederick Law Olmsted National Historic Site

A trip to Boston, Massachusetts would not be complete without a visit to its sister city, Brookline. Boston surrounds the 6-square-mile-ish suburb of Brookline on three sides and offers a fun fusion of history, culture, dining, and nature. History buffs associate Brookline with the birthplace of the 35th president of the United States John F. Kennedy while nature lovers adore meandering around its bountiful green spaces resplendent with parks and connecting with the sprawling Emerald Necklace. (Former New England Patriots quarterback Tom Brady and his former wife model Gisele Bündchen lived in a Brookline mansion for most of their marriage.)

Take it from someone who went to high school in nearby Chestnut Hill, attended college in Boston, and took my daughters to the enchanting Puppet Showplace Theater, Brookline is not only a classic New England city, but it is also an excellent destination for a day trip with lots of fun things to do for all ages. Many neighborhoods like Brookline Village and Coolidge Corner are brimming with modern and ethnic and modern eateries, kid-friendly activities, historic landmarks, green spaces, play areas, and parks. We rounded up a dozen of the best things to do in Brookline.

• ‌Perfect For:‌ Families wanting to teach their kids about American history and history buffs
• ‌Website:‌ https://www.nps.gov/jofi/index.htm
• ‌If You Go:‌ Take a stroll three blocks away to see Kennedy’s second home at the intersection of Naples Street and Abbottsford Road.

JFK’s birthplace on Beal Street in Brookline gives visitors a glimpse of how the 35th American president lived at home as a young boy. The landmark has been preserved by his mother Rose Fitzgerald Kennedy and the National Park Service. Strolling along Beals Street one can see why JFK’s parents elected to raise their family in this Boston suburb. Inside JFK’s first home, you can learn about his early life and imagine the events that shaped his life on the road to becoming the 35th President of the United States. Step inside and feel a part of American history and one of the best things to do in Brookline.

• ‌Perfect For:‌ A day of shopping, noshing, and doing cool stuff
• ‌Website:‌ www.coolidgecornershops.net
• ‌If You Go:‌ You’ll know you are there when you see the iconic clock at the intersection of Harvard and Beacon Streets

Colorful Coolidge Corner is one of my favorite places to visit in Brookline. Home of two iconic spots, Coolidge Corner Theater and Brookline Booksmith, the buzzy neighborhood has lots of unique shops and eateries and is brimming with lots of activities in Brookline. Whether you grab a corned beef sandwich at Michael’s Deli, enjoy brunch at Tatte Bakery & Cafe, or pop in for an author talk at Brookline Booksmith, you’ll relish your time in one of Brookline’s beloved neighborhoods.

• ‌Perfect For:‌ Auto and history enthusiasts
• ‌Website:‌ https://larzanderson.org
• ‌If You Go:‌ The museum is located in the Anderson Carriage House at Larz Anderson Park. Plan on spending between 45-60 minutes touring the collection.

The Larz Anderson Auto Museum is a must-do in Brookline for auto lovers. For more than 85 years, the museum has been showcasing an impressive collection of cars and is dubbed "America’s oldest car collection." Along with guided tours, the museum hosts year-round lectures, events, and programs. The museum’s architecture is gorgeous. An interesting tidbit is that Larz Anderson’s wife, Isabel, was the first woman in Massachusetts to obtain a driver’s license. One of the goals of the museum is to galvanize car enthusiasts who will surely get revved up seeing the eclectic collection.

Brookline offers a plethora of places to visit during the day. You can easily take the Massachusetts Bay Transportation Authority (MBTA) Green Line to Brookline Village and Coolidge Corner where you will find great places to shop, dine, see a movie, or visit an independent bookstore.

• ‌Perfect For:‌ Cinephiles
• ‌Website:‌ https://coolidge.org
• ‌If You Go:‌ If you love watching indie films in a cool theater, you can always return for late-night cinema on Friday and Saturday evenings shown after midnight.

Coolidge Corner Theatre has been around for nine decades and is undergoing a major capital campaign that will double the size of the treasured movie house creating a state-of-the-art center for media and film. The Art Deco theater is so much more than a place to watch movies offering classes, seminars, programs, and community partnerships. It’s the perfect place to see a classic film, a current flick, or if you’re lucky, pop into an educational or dance program. There are also special shows for children and dance programs.

• ‌Perfect For:‌ Puppet lovers of all ages, especially young children
• ‌Website:‌ https://www.puppetshowplace.org/about
• ‌If You Go:‌ Save time for fun in Brookline Village which is filled with kid-friendly places and spaces.

A trip to Brookline would not be complete without a visit to the Puppet Showplace Theater located on Station Street in Brookline Village. I recall taking my young daughters to puppet shows and watching their eyes widen with wonder watching the puppets. Puppet Showplace Theater hosts over 300 performances every year and will be celebrating 50 years in 2024. One of my favorite memories of the kid-friendly neighborhood is visiting a local toy store and enjoying ice cream in beautiful Brookline Village.

Finding the best things to do outdoors in Brookline is easy since the city is brimming with green spaces, parks, playgrounds, and an abundance of ways to celebrate Mother Nature. Whether you follow the Emerald Necklace, spend a day sledding or delight in lunch at picnic tables in Larz Anderson Park, enjoy a jog around Brookline Reservoir, or pick up some posies or plants at Allandale Farm, you will find a bevy of ways to enjoy the outdoors in Brookline.

• ‌Perfect For:‌ Four-season family fun
• ‌Website:‌ https://www.brooklinema.gov/facilities/facility/details/larz-anderson-park-87
• ‌If You Go:‌ Bring your ice skates in the winter and a lunch to munch at the picnic tables. Larz Anderson Park is splendid in all seasons. You can bring the dog too!

Larz Anderson Park always tops the list of must-see places in Boston and Brookline. The largest park in Boston is listed on the National Register of Historic Places and is a great place to spend the day in any season. Here you will discover fields to roam and play basketball and softball, community gardens, a green dog park, a skating rink, picnic tables, ponds, and plenty of walkways, trails, and ponds. Kids love skating on the ice rink and sledding down rolling hills in the winter.

If you love walking around Boston Common, you’ll adore spending time at Larz Anderson Park where you can see the skyline of Boston, enjoy the lovely grounds, or take a guided tour of Larz Anderson Auto Museum housed within the Carriage House.

• ‌Perfect For:‌ Runners and joggers
• ‌Website:‌ https://www.brooklinema.gov/facilities/facility/details/Brookline-Reservoir-Park-81
• ‌If You Go:‌ Lace up your sneakers for a one-mile trail.

Brookline Reservoir Park is one of my favorite places to take a quick jog and enjoy a beautiful view of the Boston skyline. The one-mile loop offers a quiet place to reflect and enjoy nature. If you’re visiting Boston and want to take a quiet break, it is the perfect spot to recalibrate.

• ‌Perfect For:‌ People who love plants and nature
• ‌Website:‌ https://allandalefarm.com
• ‌If You Go:‌ Check out the fun community activities.

Nature lovers will delight in discovering Allendale Farm which is in both Boston and Brookline. One of the oldest continuous working farms in America, Allandale Farm features a farm stand, a garden center (voted Best of Boston 2023), and a roster of fun activities like hay rides, yoga, bird watching, and pumpkin and Christmas tree picking.

If you are looking for what to do in Brookline at night, you'll discover plenty of bars and restaurants to grab drinks or dinner. One of the best things to do in Brookline at night is enjoy a weird late-night movie at Coolidge Theatre's After Midnite or browse through the books at Brookline Booksmith. If you time it right, you can see a great author talk at the independent bookstore.

• ‌Perfect For:‌ A late date night
• ‌Website:‌ https://coolidge.org/programs/after-midnite
• ‌If You Go:‌ Be prepared to have a sleepless night.

The iconic Coolidge Corner Theatre offers late-night programs after midnight on Friday and Saturday nights. The eclectic roster of screenings includes weird, scary, and surprising movies. You don’t want to go alone!

• ‌Perfect For:‌ Bookworms
• ‌Website:‌ Brookline Booksmith
• ‌If You Go:‌ Check the calendar to see who’s in store when you’re in town

Brookline Booksmith is one of Boston’s beloved spots to browse books, meet local and national authors, and discover great gifts and inspiration. Get lost in the shelves of the independent bookstore that has been a favorite spot to browse for more than six decades.

One of the best things about Brookline is that there are so many things to do that don’t cost a cent. Whether you visit one of the art galleries, stroll along the Emerald Necklace, pop by a park or playground, or visit Brookline Farmer’s Market, Brookline Booksmith, or one of the National Historic Sites, your life will be richer for the visit.

• ‌Perfect For:‌ Getting produce for the night's meal.
• ‌Website:‌ www.brooklinefarmersmarket.com
• ‌If You Go:‌ You’ll find the market right behind the Coolidge Corner Theatre

If you’re visiting Brookline between June and Thanksgiving, be sure to check out the Brookline Farmer’s Market on Thursdays between 1:30 to 6:30 p.m. Here you’ll find lots of local fruits, veggies, meats, and treats along with lovely wares from local artisans.

• ‌Perfect For:‌ Lovers of landscape architecture and history
• ‌Website:‌ www.nps.gov/places/frederick-law-olmsted-national-historic-site
• ‌If You Go:‌ Take note of how many designs Olmsted inspired

Brookline was the home of Frederick Law Olmsted, the father of landscape architecture. The old farmhouse and grounds are now a National Historic Site. It is breathtaking to see where Omstead lived and worked. You won’t have enough time to go through the almost one million records of Olmsted firm designs, but the visit will give you insight into the man who designed spaces including New York’s Central Park and Boston’s Emerald Necklace.

It was hard to narrow down the best things to do in Brookline to a dozen. If you follow the Emerald Necklace or take the MBTA's Green Line, you'll be sure to find lots of things to do in Boston's beautiful sister city.