Things to do in Brookline

    Discover amazing Brookline activities and premium in-home experiences.

    Bordering Boston but worlds apart, Brookline, MA is a leafy enclave where tree-lined streets cradle stately homes and cozy cafes hum with neighborly warmth. Here, history lingers beneath grand elms and in colonial architecture, creating an inviting tapestry that feels both timeless and undeniably alive. In Brookline, urban energy softens into village charm—encouraging you to slow down and savor each moment’s quiet elegance.

    Popular Activities in Brookline

    Hands-On Dumpling Making Class in Boston

    Master folding techniques and enjoy your own dumplings in a fun 2-hour cooking session.

    4.7 404 reviews
    $88/ person

    Boston Freedom Trail Walking Tour with Guide

    Immerse yourself in Boston's Freedom Trail chronicle with a small-group, storyteller-led walk.

    5.0 267 reviews
    $45/ person

    Somerville Food Tour: 5 Bites in Union Square

    Taste five diverse bites in Union Square while exploring its vibrant history with a local guide

    4.9 126 reviews
    $75/ person

    Harvard Square Chocolate Tasting & History Tour

    Sample decadent treats and learn chocolate history while exploring historic Harvard Square.

    4.9 126 reviews
    $50/ person

    Behind the Scenes Director's Tour in Salem

    Enjoy a small-group, behind-the-scenes museum tour with expert docent and complimentary digital photos.

    4.9 2.1K reviews
    $20/ person

    Haunted Salem After Dark Walking Tour

    Explore Salem’s historic streets after dark and hear spine-tingling tales from a local guide.

    4.6 246 reviews
    $20/ person

    Boston Photo Tour: Back Bay & Beacon Hill

    Capture stunning images while exploring Back Bay, the Public Garden, and Beacon Hill with expert photo tips

    4.9 96 reviews
    $25/ person

    Historic Boston Harbor Sail with Landmark Views

    Sail an 80-foot classic schooner and admire Boston Harbor landmarks

    4.8 469 reviews
    $38/ person

    Boston Harbor Cruise: 90 Min Skyline & Landmarks

    Discover Boston’s skyline and historic landmarks on a relaxing 60–90 minute harbor cruise.

    4.8 469 reviews
    $32/ person

    Boston Sunset Cruise on 1920s Vintage Yacht

    Savor evening skyline views with light commentary and music aboard a classic 1920s-style yacht.

    4.8 469 reviews
    $60/ person

    Boston & Cambridge E-Scooter Tour with Lunch

    Glide on electric scooters through historic Boston and innovative Cambridge with lunch and photos included

    4.9 2.8K reviews
    $179/ person

    Effortless Boston Segway Tour: 15+ Landmarks

    Cover Boston's key landmarks, skyline views, and Freedom Trail sites effortlessly on a fun Segway ride

    4.9 2.8K reviews
    $89/ person

    Historic Boston in 1 Hour: Guided Scooter Tour

    Cover Boston's top historic sites on an easy electric scooter, guided and photo-ready in only an hour.

    4.9 2.8K reviews
    $59/ person

    Boston Freedom Trail Segway Tour (1 Hour)

    Glide along Boston's Freedom Trail on a Segway to see iconic landmarks in just one hour

    4.9 2.8K reviews
    $62/ person

    Lexington Revolutionary War Trolley Tour

    Discover Colonial-era Lexington on a 90-minute guided trolley ride led by costumed historians.

    4.5 386 reviews
    $20/ person

    Salem Harbor Sunset Sail on 1812 Schooner

    Watch Salem Sound glow at day’s end while you help raise the sails and toast the sunset with a relaxed drink.

    5.0 520 reviews
    $49/ person

    Explore the Charms of Brookline

    Brookline is a vibrant town where historic charm meets modern allure, offering visitors an array of experiences that feel both timeless and fresh. Stroll through its tree-lined streets, where sunlight filters through lush canopies, casting dappled shadows on beautifully preserved Victorian homes. The town’s proximity to Boston provides easy access to urban adventures while maintaining its own unique character with local boutiques, quaint cafes, and an inviting community atmosphere.

    For those looking to immerse themselves in culture and history, a visit to the John F. Kennedy National Historic Site offers a glimpse into the early life of America’s 35th president. Art enthusiasts will appreciate the nearby Museum of Fine Arts or can explore contemporary exhibits at local galleries scattered throughout Brookline Village. As seasons change, so do the activities; from enjoying summer concerts at Larz Anderson Park with panoramic views of Boston's skyline to savoring autumn walks along forested trails in Olmsted Park.

    Culinary delights await around every corner—whether you’re sampling global flavors at Coolidge Corner or indulging in farm-to-table dining experiences that highlight New England's bounty. In winter months, cozy up with a hot chocolate from one of many artisanal coffee shops before catching an indie film at the historic Coolidge Corner Theatre. With its blend of cultural richness and small-town warmth, Brookline invites exploration and promises memories as enduring as its storied past.

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