Things to Do in Brookline, MA

Brookline, Mass., is a charming town just minutes from downtown Boston, offering a perfect blend of urban convenience and suburban tranquility. Known for its tree-lined streets, historic architecture, and vibrant cultural scene, Brookline is a community that balances the hustle and bustle of city life with the peacefulness of residential neighborhoods. Its rich history, diverse dining options, and abundance of parks make it an attractive destination for visitors and locals.

Whether you’re strolling through its scenic parks, exploring unique shops, or immersing yourself in its historic landmarks, Brookline offers countless things to do that showcase the town’s unique character and welcoming atmosphere.

One of the top things to do in Brookline is visiting the John F. Kennedy National Historic Site. This modest home is the birthplace of President John F. Kennedy and offers a glimpse into the early life of one of America’s most beloved leaders. Located in a quiet residential neighborhood, this historic site is a must-visit for history enthusiasts. The guided tours provide a personal and intimate experience of JFK’s childhood home and the neighborhood where he spent his early years.

Coolidge Corner is one of the busiest and most beloved areas in Brookline. It’s a lively district filled with shops, cafes, and restaurants, making it a great place to explore on foot. There’s always something happening here, whether it’s a community event, a live performance, or a local market. In addition to shopping and dining, Coolidge Corner is home to the Coolidge Corner Theatre, one of the oldest art-deco movie theaters in the country. Catching a film here is one of the most popular things to do in Brookline, thanks to the theater’s unique atmosphere and diverse selection of indie films.

Brookline Booksmith is an iconic independent bookstore located in Coolidge Corner. It offers many books across various genres, gifts, stationery, and more. The bookstore regularly hosts author events, readings, and book signings, making it a cultural hub for book lovers in Brookline. Spending time at the Brookline Booksmith is one of the best things to do in Brookline for those who love literature. Whether you’re looking for the latest bestseller or a unique gift, this bookstore has something for everyone.

Larz Anderson Park is one of Brookline's largest and most beautiful parks. Its sprawling green spaces, scenic views, and historic structures make it a perfect spot for a relaxing afternoon. The park offers picnic areas, walking trails, and a pond where you can enjoy paddle boating in the summer. During the winter, the park becomes a popular spot for ice skating. Larz Anderson Park is also home to the Larz Anderson Auto Museum, where you can explore a fascinating collection of vintage cars.

Frederick Law Olmsted is known as the father of American landscape architecture, and his home and office, Fairsted, is located in Brookline. The Frederick Law Olmsted National Historic Site offers guided tours where visitors can learn about his life and influence on American parks and public spaces, including New York’s Central Park and Boston’s Emerald Necklace. The site includes exhibits showcasing Olmsted’s original plans and designs and the grounds of his former home. It’s a fascinating place to visit, especially for those interested in history, architecture, and urban planning.

The Puppet Showplace Theater in Brookline Village is a unique attraction and one of the oldest puppet theaters in the country. It offers shows for children and adults, ranging from traditional puppetry to modern performances. The theater also hosts workshops, making it a fun and interactive experience. A visit to the Puppet Showplace Theater is one of the more creative things to do in Brookline, perfect for families looking to enjoy a fun afternoon or anyone interested in puppetry.

Washington Square in Brookline is a charming neighborhood with a mix of small businesses, boutiques, and restaurants. It’s a quieter alternative to Coolidge Corner but offers plenty of dining and shopping options. Many local cafes and eateries in Washington Square provide outdoor seating, making it a great place to enjoy a meal on a sunny day. With outdoor markets and community gatherings, it’s a wonderful place to explore, whether you’re grabbing a coffee or enjoying a casual dinner with friends.

The Brookline Farmers’ Market, held seasonally from June to November, is one of the best places to find fresh, locally grown produce and artisanal goods. Located in Coolidge Corner, the market features a variety of vendors offering everything from fruits and vegetables to baked goods and handmade crafts. The market is a great way to support local farmers and businesses while enjoying the vibrant community atmosphere.

Longwood Playground is a family-friendly park located in the Longwood neighborhood of Brookline. The playground features modern equipment, a splash pad for warm days, and plenty of open space for running around. It’s an ideal spot for families with young children to spend a few hours outdoors. In addition to the playground, the park has shaded picnic areas and benches where parents can relax while the kids play.

Brookline boasts a vibrant and diverse dining scene, offering a wide range of culinary options that cater to every taste. In Coolidge Corner, you’ll find Zaftigs Delicatessen, a beloved spot known for its classic Jewish comfort food, including hearty sandwiches and matzo ball soup. For something more upscale, head to La Morra in Washington Square, where Northern Italian cuisine shines through handmade pasta and braised meats. For those in the mood for Mediterranean flavors, Tatte Bakery & Café offers fresh salads, sandwiches, and pastries in a cozy setting. The Abbey in Washington Square is another local favorite, serving pub fare with a modern twist and a great selection of craft beers. Bar Vlaha was recently honored as one of Boston's best restaurants by Boston Magazine for its unique focus on the traditional cuisine of the Vlach people from northern Greece.

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