What to do in Brookline, MA

Activities, attractions and tours

Photo by Din Kime
Photo by Perry Grossman
Photo by Madeline Yost
Photo by Madeline Yost
Photo by Shannon Willitts

Explore thousands of activities with free cancellation and no added fees.

Design your experience with airport transfers, excursions, day tours & more.

Get an insider's look in what to book before you travel.


Most fun & popular experiences in Brookline

Tours & day trips

See all 259 activities

Private & custom tours

See all 52 activities

Food, drink & nightlife

See all 41 activities

Classes & workshops

See all 8 activities

What to do in Brookline


Popular places to visit

Explore areas of Brookline

Default Image

Chestnut Hill

Well liked for its restaurants and sporting events, Chestnut Hill is worth a visit. Check out the variety of things to see and do like Alumni Stadium and Chestnut Hill Reservoir, and jump on the metro at Chestnut Hill Station to get around the city.

Chestnut Hill
Default Image

Cleveland Circle

4/5(4 area reviews)

Cleveland Circle is a destination travellers like for its restaurants, and you might hop aboard the metro at Cleveland Circle Station or Reservoir Station to explore sights like Chestnut Hill Reservoir.

Cleveland Circle
Default Image

North Brookline

While you're in North Brookline, take in top sights like Coolidge Corner Theatre and jump on the metro at Coolidge Corner Station to see more of the city.

North Brookline
Default Image

Coolidge Corner South Side

When in Coolidge Corner South Side and the surrounding area, you'll want to check out sights like Fenway Park or Coolidge Corner Theatre and hop on the metro to see more of the city at Coolidge Corner Station or Summit Av. Station.

Coolidge Corner South Side
Default Image

Longwood

While you're strolling through Longwood, you may want to check out the coffee shops and architecture. If you want to see more of the area, hop on the metro at Longwood Station or Hawes St. Station.

Longwood
Default Image

High Street Hill

When in High Street Hill, you can plan a visit to Fenway Park and Coolidge Corner Theatre, some noteworthy sights in the nearby area.

High Street Hill

Day trip destinations from Brookline