Want a peaceful retreat near Boston with historic charm and leafy streets? Head to Brookline! Known for its tree-lined avenues, cultural institutions, and connection to President John F. Kennedy, Brookline is a refined and walkable town with easy access to Boston. Explore elegant neighborhoods, cozy cafés, and museums in this uniquely urban-suburban destination.

Best Time to Visit

The best time to visit Brookline is during spring and fall (April–June and September–October), when the weather is mild and perfect for walking tours and park visits. Summer is ideal for outdoor patios and festivals, while winter is quieter with snow-dusted charm.

How to Get There

  • By Subway: The MBTA Green Line C and D branches serve multiple stops in Brookline, including Coolidge Corner and Brookline Village.
  • By Air: Logan International Airport (BOS) is about 20–30 minutes away by car or public transit.
  • By Car: Brookline is just a few miles west of downtown Boston and accessible via Route 9 or the Mass Pike (I-90).

Where to Stay

  • Courtyard by Marriott Boston Brookline – Centrally located with modern amenities and easy T access.
  • Arcadian Hotel Brookline – Stylish boutique hotel with mid-century modern flair near Coolidge Corner.
  • Bertram Inn – Elegant bed & breakfast in a historic brownstone with vintage charm and homemade breakfast.

Top Attractions

Walk Through History at the John Fitzgerald Kennedy National Historic Site

Walk Through History at the John Fitzgerald Kennedy National Historic Site

© NPS Photo

For those interested in stepping into the birth home of President John F. Kennedy, his mother, Rose, has lovingly restored that home to its former state. Guests to the home will be ushered into the basement, where they will find a gift shop. Afterward, the guests can take a self-guided or ranger-guided tour through the home. Though the top floor has not been renovated and is used as attic space, the remainder of the home, including servants’ quarters, has been restored to about the exact time of JFK’s birth (which was at home). Guests can see actual artifacts that belonged to the family, as well as family photos throughout the home.

John Fitzgerald Kennedy National Historic Site, 83 Beals Street, Brookline, MA 02446, Phone: 617-566-7937

Picnic or Play with Panoramic Views at Larz Anderson Park

Picnic or Play with Panoramic Views at Larz Anderson Park

© GCapture/stock.adobe.com

Massachusettes summers are fairly short, so when you have good weather, consider getting to one of the local parks to enjoy some outdoor fun. Larz Anderson Park is the largest park in Brookline, and because of its size, it offers great views of Boston at the top of the hill. Visitors can enjoy picnics and hikes on the grounds. Along with a baseball field, there is a community garden, a playground, and a dog park. If you’re visiting in the colder months, you can still enjoy the park. There is an outdoor skating rink on site every winter.

Goddard Avenue & Newton Street, Brookline, MA 02445, Phone: 617-879-5650

Activities and Attractions for Couples:

Catch a Film with Charm at the Coolidge Corner Theatre

Catch a Film with Charm at the Coolidge Corner Theatre

© whyframeshot/stock.adobe.com

Built in 1906 as a church, Coolidge Corner Theatre became a privately-owned cinema in 1933. Since it’s designation, it has split the one screen into four different screens. Today’s patrons can enjoy several movie selections, as they rotate. Coolidge Corner shows documentaries, indie films, animation, and new releases. If you’re interested in going, check out the large listing of shows on their website. Often, they label movies by group, for instance: new releases, cinema jukebox, off the couch, box office babies, and after midnite. These are just a few of the programs offered, so you’ll always want to check back.

290 Harvard Street, Brookline, MA 02446, Phone: 617-734-2501

If you are traveling with kids:

Explore Vintage Rides at the Larz Anderson Auto Museum

Explore Vintage Rides at the Larz Anderson Auto Museum

© Larz Anderson Auto Museum

As part of the Larz Anderson Park, you’ll find the Larz Anderson Auto Museum at the Anderson Carriage House. Visitors can experience the largest auto collection in America only ten minutes away from Boston. Special programs are held throughout the month, so no matter when you visit, you’re bound to have a great time. Consider checking out a themed car day, like the British Car Day or the American Car & Truck Day. Visit the lawn shows on the weekends, or take part in cars & coffee Sunday mornings, where car-enthusiasts meet to admire and talk cars while sipping fresh coffee.

15 Newton Street, Brookline, MA 02445, Phone: 617-522-6547

Learn About Landscape Legacy at the Frederick Law Olmsted National Historic Site

Learn About Landscape Legacy at the Frederick Law Olmsted National Historic Site

© NPS Photo

Frederick Law Olmstead was the world’s first full-size professional landscape architect. He purchased this home and redesigned it to better suit his family’s needs. When the park was acquired by the National Park Service, it was restored to appear as it did in 1930. Tours for visitors are open from May to September, though the gardens are open year-round. You can talk a self- or ranger-guided tour, but the Design Office is only available on a guided tour. If you’d like to visit during one of the lectures or talks, be sure to check with the Historic Site website to plan for special events.

Frederick Law Olmsted National Historic Site, 99 Warren Street, Brookline, MA 02445, Phone: 617-566-1689

Shop Fresh and Local at Historic Allandale Farm

Shop Fresh and Local at Historic Allandale Farm

© Allandale Farm

Whether you’re a local or a visitor, Allandale Farm is the place to find your spring and summer garden needs. If you’re a visitor, remember that some plants will not do well in foreign climates and soils, so purchase wisely. For all other gardening needs, Allendale has you covered. Though farming is their primary mission, visitors can check out some of the programs and events sponsored and held on the farm. For instance, Story Time on the Hill is held every Wednesday during the summer, or edible plant and knife sharpening talks and demonstrations. Visiting specialists, like fishermen, bring their specialties to sell while fresh.

259 Allandale Road, Chestnut Hill, MA 02467, Phone: 617-524-1531

Grab a Crispy Slice at Stoked Wood Fired Pizza Co.

Grab a Crispy Slice at Stoked Wood Fired Pizza Co.

© Stoked Wood Fired Pizza Co.

Who doesn’t love pizza? When you’re ready for some wood-fired pizza, Stoked Wood Fired Pizza Co. is the place to go. Plenty of fresh ingredients pull together to make the Stoked pizzas. Working with Lilliput Farms, freshly grown ingredients are delivered daily to prepare only the freshest pizzas and recipes available. If you choose to eat at this gourmet pizza place, consider checking out some of the other delights beyond the wood-fired oven, such as waffle fries with chipotle aioli, crunchy cauliflower bites, and wings. Be sure to order one of the many specialty milkshakes with your pizza. Stoked also offers gluten-free and vegan options.

1632 Beacon Street, Brookline, MA 02446, Phone: 617-879-0707

Slurp Authentic Sapporo-Style Noodles at Ganko Ittetsu Ramen

Slurp Authentic Sapporo-Style Noodles at Ganko Ittetsu Ramen

© somegirl/stock.adobe.com

For a taste of Japan, head over to Ganko Ittetsu Ramen. In 2016, they were listed as one the Boston Magazine’s top new restaurants. Serving the Sapporo region’s style of ramen, guests will enjoy the wok-made recipes. Enjoy ramen noodle bowls that combine broth/sauce, ramen, and delicious ingredients. Most dishes include multiple types of meat and a 5-minute egg for added protein and creaminess. Using the Sapporo method allows the chef to heat the wok to a much higher temperature, ensuring the deepening of flavors. The tastes will be so grand that you’ll be tipping the bowl for the last drops of broth as they do in Japan.

318 Harvard Street, Brookline, MA 02446, Phone: 617-730-8100

Must-see if you are a first-time visitor:

  • Brookline Booksmith – Iconic indie bookstore with curated titles, author events, and quirky gifts.
  • Emerald Necklace Parks – Walk or bike through green spaces like Olmsted Park and The Riverway, designed by Frederick Law Olmsted.

Where to Eat

  • Zaftigs Delicatessen – Beloved Jewish deli with huge sandwiches, matzo ball soup, and hearty breakfasts.
  • Barcelona Wine Bar – Lively tapas bar with Spanish-inspired small plates, craft cocktails, and a vibrant patio scene.
  • Ganko Ittetsu Ramen – Cozy, casual ramen shop tucked inside Coolidge Corner Arcade with bold flavors and authentic broth.

If you are interested in local events:

  • Brookline Porchfest (June) – Local musicians perform on porches throughout town for a free grassroots music festival.
  • Coolidge After Midnite (Fridays/Saturdays) – Cult classics, horror, and genre films screened late at the Coolidge Theatre.
  • Brookline Day (Fall) – Family-friendly celebration in Larz Anderson Park with games, food trucks, music, and crafts.

If you are looking for unique day trips within 30 Minutes of Brookline, Massachusetts:

  • Boston’s Back Bay (10–15 min) – Visit the Boston Public Library, shop on Newbury Street, or stroll the Charles River Esplanade.
  • Fenway Park (10 min) – Catch a Red Sox game or tour one of baseball’s most historic stadiums.
  • Cambridge (20 min) – Explore Harvard Square, MIT, museums, and funky shops and restaurants.
  • Jamaica Plain (10–15 min) – Stroll Arnold Arboretum, bike around Jamaica Pond, or browse hipster cafés and vintage stores.
  • Newton (15–20 min) – Quiet suburban neighbor with scenic walking trails, upscale dining, and local museums.
  • Chestnut Hill Reservoir (10 min) – Peaceful loop trail around a historic reservoir with skyline views and birdwatching.

Frequently Asked Questions:

  • Question: Where is Brookline located?
    Answer: Brookline is located right outside of Boston, MA, offering proximity to the big city.
  • Question: When was Brookline established?
    Answer: Brookline was established in 1638.
  • Question: What historical significance does Brookline have?
    Answer: Brookline was the birthplace of President John F. Kennedy.
  • Question: What attractions does Brookline offer?
    Answer: Brookline offers plenty of historic sites to visit and exotic cuisine from around the world.
  • Question: What is the population of Brookline?
    Answer: Brookline has a population of over 58,000.
  • Question: Why is Brookline a great place to stay when visiting Boston?
    Answer: Brookline provides a suburban feel while being close to Boston, making it a great place to stay.
  • Question: What communities are prominent in Brookline?
    Answer: Brookline is home to large Jewish and Greek Orthodox communities.

At a Glance:


Best Time to Visit Places to Stay Tips for Visiting
Spring (March-May) – Mild temperatures and blooming flowers, great for exploring parks. The Arcadian Hotel Brookline – A stylish and comfortable stay near public transit. Visit Larz Anderson Park – Enjoy open green spaces, picnic spots, and scenic city views.
Summer (June-August) – Warm and lively, ideal for outdoor dining and sightseeing. Hilton Garden Inn Boston Brookline – A modern hotel with easy access to downtown Boston. Explore Coolidge Corner – Shop at local boutiques and catch a film at the historic Coolidge Corner Theatre.
Fall (September-November) – Crisp air and stunning fall foliage, perfect for walking tours. The Bertram Inn – A charming and historic bed-and-breakfast. Tour the John F. Kennedy National Historic Site – Learn about JFK’s early years in Brookline.

Plan Your Trip


Table of Contents: