17 Fun Things To Do In Brookline MA Massachusetts

Things To Do In Brookline MA

Nestled just outside the vibrant city of Boston, Brookline, Massachusetts, offers a unique blend of historical charm, cultural richness, and recreational opportunities. Whether you’re a history buff, an art enthusiast, or someone who enjoys the outdoors, Brookline has something for everyone. In this guide, we’ll take you on a journey through the top things to do in this picturesque town, ensuring your visit is both memorable and fulfilling.

  1. Discover Coolidge Corner:

Start your exploration in Coolidge Corner, the heart of Brookline. This bustling neighborhood boasts a variety of shops, cafes, and boutiques. Take a leisurely stroll along Harvard Street, where you’ll find a mix of trendy stores and classic New England architecture. Don’t forget to stop by the iconic Coolidge Corner Theatre, a historic cinema that showcases independent and foreign films.

  1. Explore The Larz Anderson Auto Museum:

Car enthusiasts will find paradise at the Larz Anderson Auto Museum. Home to an impressive collection of vintage automobiles, this museum provides a fascinating glimpse into the history of the automotive world. From classic cars to rare models, the exhibits are sure to captivate visitors of all ages.

  1. Visit the John F. Kennedy National Historic Site:

Dive into the rich political history of the United States by exploring the John F. Kennedy National Historic Site. Located in Brookline, this site preserves the birthplace and childhood home of the 35th President. Guided tours offer insight into Kennedy’s early life and the events that shaped his presidency.

  1. Enjoy Nature at Olmsted Park:

Escape the hustle and bustle of city life by spending a relaxing day in Olmsted Park. Designed by the renowned landscape architect Frederick Law Olmsted, this green oasis offers walking and biking paths, serene ponds, and picturesque bridges. It’s the perfect spot for a family picnic or a quiet afternoon of contemplation.

  1. Cultural Immersion at the Brookline Arts Center:

Immerse yourself in Brookline’s vibrant arts scene at the Brookline Arts Center. Featuring rotating exhibitions, art classes, and workshops, the center provides a platform for local artists to showcase their talents. Whether you’re an art enthusiast or a budding creative, there’s something for everyone here.

  1. Indulge in Culinary Delights:

Brookline is a haven for foodies, with a diverse range of culinary options. From cozy cafes to upscale restaurants, the town’s dining scene caters to every palate. Be sure to explore local favorites and international cuisines that reflect the town’s cultural diversity.

  1. Rejuvenate at The Public Garden:

For a serene escape, visit The Public Garden, a meticulously maintained green space in the heart of Brookline. Stroll through beautifully landscaped gardens, pause by the soothing fountains, and enjoy a moment of tranquility away from the urban buzz.

  1. Brookline Booksmith:

Book lovers rejoice at the Brookline Booksmith, an independent bookstore that has been a local favorite since 1961. Browse through the shelves filled with a diverse selection of books, attend author events, and explore unique literary finds. It’s a haven for those who appreciate the written word.

  1. Coolidge Corner Theatre After Midnight:

Experience cinema in a whole new way at Coolidge Corner Theatre After Midnight events. From cult classics to special screenings, these late-night showings offer a unique and immersive movie experience. Grab some popcorn and enjoy a film in a lively and nostalgic atmosphere.

  1. Longwood Medical Area:

For those interested in healthcare and medical history, the Longwood Medical Area is a fascinating destination. Home to renowned medical institutions like Harvard Medical School and the Longwood Medical and Academic Area, you can explore the cutting-edge developments in the field of medicine.

  1. Putterham Grille:

Delight your taste buds at Putterham Grille, a local gem known for its delicious brunch offerings and cozy ambiance. Whether you’re craving classic breakfast fare or inventive brunch creations, this spot is perfect for a leisurely morning meal.

  1. Brookline Reservoir Park:

Enjoy a day outdoors at the Brookline Reservoir Park. This scenic location offers walking and jogging trails around the reservoir, providing a peaceful escape surrounded by nature. The park is particularly beautiful during the fall when the foliage paints the landscape in vibrant colors.

  1. The Puppet Showplace Theater:

Embrace the arts in a unique form at The Puppet Showplace Theater. Dedicated to the art of puppetry, this venue hosts performances for audiences of all ages. Check the schedule for puppet shows, workshops, and events that bring stories to life through the enchanting world of puppetry.

  1. Washington Square:

Washington Square is a charming neighborhood in Brookline with a village-like atmosphere. Explore the tree-lined streets, boutique shops, and cozy cafes. The square is also known for its diverse range of restaurants, offering cuisines from around the world.

  1. Cypress Street Playground:

If you’re traveling with family, head to Cypress Street Playground. This kid-friendly park features playground equipment, open spaces for picnics, and a basketball court. It’s a great spot for families to unwind and let children play.

  1. Brookline Farmer’s Market:

Experience the local flavors at the Brookline Farmer’s Market. Held seasonally, the market showcases fresh produce, handmade crafts, and a variety of artisanal goods. It’s an excellent opportunity to support local vendors and indulge in the region’s culinary offerings.

  1. Brookline Historical Society:

Delve deeper into Brookline’s past at the Brookline Historical Society. Explore exhibits, attend lectures, and gain insights into the town’s history and development. It’s a fascinating journey through time for history enthusiasts.


Brookline, Massachusetts, may be a small town, but its charm and diversity make it a must-visit destination. Whether you’re interested in history, culture, or simply enjoying the outdoors, Brookline offers a delightful array of experiences. So, pack your bags, lace up your walking shoes, and get ready to discover the hidden gems of this New England gem. Your adventure in Brookline awaits!

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