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The Top Attractions in and Around Brookline, MA

Elisabeth Preis March 17, 2025


Brookline, Massachusetts, is a town that blends historical charm with modern attractions. Whether you’re a long-time resident or visiting for the first time, there’s no shortage of things to see and do. From significant historical sites to scenic parks and cultural experiences, Brookline offers a diverse array of attractions that appeal to all interests.

John F. Kennedy National Historic Site

Step into history at the birthplace of the 35th President of the United States. Located at 83 Beals Street, this preserved home provides an intimate glimpse into John F. Kennedy’s early life. Guided tours take visitors through rooms filled with original furnishings and personal items from the Kennedy family. The site also includes an audio tour, narrated by Rose Kennedy, offering personal stories about the family's time in Brookline.

For history enthusiasts, this landmark is an essential stop, highlighting the early influences that shaped one of America’s most iconic leaders.

Coolidge Corner Theatre

Brookline’s Coolidge Corner Theatre is more than just a place to watch movies—it’s a historic and cultural institution. First opened in 1933, this Art Deco cinema showcases independent films, documentaries, and classic movies. Special screenings often include discussions with filmmakers, themed events, and midnight showings of cult favorites.

It’s a must-visit for film lovers who appreciate a mix of mainstream and arthouse cinema, all presented in a beautifully restored historic setting.

Larz Anderson Park and Auto Museum

One of Brookline’s largest green spaces, Larz Anderson Park, offers rolling hills, walking trails, and stunning city views. This 64-acre park is a favorite for picnics, sledding in the winter, and simply enjoying the outdoors.

The Larz Anderson Auto Museum, located within the park, houses the oldest car collection in the United States. Visitors can explore vintage automobiles and rotating exhibits that delve into the history of car design and innovation.

The Shops and Restaurants of Coolidge Corner

No visit to Brookline is complete without exploring Coolidge Corner. This bustling area is known for its mix of local boutiques, bookstores, and restaurants offering global cuisine. Favorites include:

  • Zaftigs Delicatessen – A go-to spot for classic Jewish deli fare.
  • Brookline Booksmith – A beloved independent bookstore with an extensive selection and frequent author events.
  • Otto Pizza – Known for its creative toppings and crispy crusts.
Whether you’re shopping for unique gifts or grabbing a bite to eat, Coolidge Corner has something for everyone.

Frederick Law Olmsted National Historic Site

Brookline is home to "Fairsted," the former residence and office of Frederick Law Olmsted, the father of American landscape architecture. This site offers guided tours that explore Olmsted’s work designing some of the most famous parks in the country, including Central Park in New York City and the Emerald Necklace in Boston.

Visitors can see where Olmsted and his team developed their landscape designs, with original blueprints and sketches still on display. For those interested in architecture and urban planning, this is a fascinating stop.

Olmsted Park

Part of Boston’s famous Emerald Necklace, Olmsted Park is a picturesque escape within Brookline. With walking paths, ponds, and scenic bridges, this park is perfect for a morning jog, an afternoon picnic, or a leisurely walk.

The best part? It’s an ideal place to relax while still being close to the energy of the city. Birdwatchers and nature enthusiasts will appreciate the diverse wildlife that calls this park home.

Puppet Showplace Theater

Looking for something unique? The Puppet Showplace Theater is a hidden gem that offers performances for all ages. As the only dedicated puppet theater in New England, it hosts a variety of shows, from traditional hand puppetry to modern marionette performances.

The theater also provides workshops and educational programs, making it a fun and interactive experience for children and families.

Brookline Reservoir Park

A lesser-known but equally charming spot, Brookline Reservoir Park offers a scenic walking loop around a calm body of water. This peaceful retreat is great for jogging, dog walking, or simply taking in the fresh air. The view of the Boston skyline from certain spots along the trail makes it a favorite for photographers and nature lovers alike.

The Public Library of Brookline

For book lovers, the Public Library of Brookline is more than just a place to check out books. This historic library offers author talks, community events, and cozy reading spaces. The main branch, housed in a grand building with beautiful architectural details, is a welcoming space for both locals and visitors.

The Larz Anderson Skating Rink

During the winter months, the Larz Anderson Skating Rink is a must-visit attraction. Located within Larz Anderson Park, the outdoor rink provides a charming setting for ice skating, whether you're a beginner or an experienced skater. The rink offers rentals and public skating sessions, making it a great activity for families and friends.

Reach Out to Elisabeth Preis

If you’re considering making Brookline your home, Elisabeth Preis is ready to assist with all your real estate needs. With extensive knowledge of the area and a deep understanding of the market, she can help you find the perfect home that fits your lifestyle. Whether you’re buying, selling, or just starting to explore your options, Elisabeth offers expert guidance and personalized service.

Contact Elisabeth Preis today to start your real estate journey in Brookline, MA. Let her expertise help you navigate the market and find a place to call home in this exceptional town.

Search homes for sale in Brookline here.



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