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Things To Do in Chestnut Hill, Massachusetts

Boston College – Gasson Hall

An iconic Collegiate Gothic landmark designed by Charles Donagh Maginnis, Gasson Hall features a soaring bell tower and majestic rotunda—ideal for campus strolls and photography.

Gasson Hall at Boston College

Phone: +1617‑552‑8000

Official site

 

Metropolitan Waterworks Museum

Set inside an 1887 Richardsonian Romanesque pumping station, this museum features massive steam pumps and interactive exhibits about Boston’s water history.

Metropolitan Waterworks Museum exterior

Phone: +1617‑926‑8148

Official site

 

Chestnut Hill Reservoir

A serene 1.5‑mile loop around the reservoir offers walking, jogging, birdwatching, and beautiful waterfront views—especially spectacular in autumn.

Chestnut Hill Reservoir

Phone: (no direct office)

More info

 

Chestnut Hill Reservation

A historic 120-acre state park designed by Olmsted’s son, featuring trails around the reservoir, skating rinks, and a recreation center—all nestled within urban Boston.

Chestnut Hill Reservation

Phone: +1617‑727‑5290

Official site

 

Hammond Pond Reservation

A 59-acre woodland with a scenic pond, woodland trails, preaching rock formations, and routes that connect to nearby conservation areas—great for walkers and climbers.

Hammond Pond Reservation

Phone: (no direct office)

Official site

 

Allandale Farm

The last working farm in Chestnut Hill, offering pick-your-own produce, greenhouse plants, pond views, and seasonal family events year-round.

Allandale Farm Pond

Phone: +1617‑524‑1531

Official site

 

Morris Arboretum & Gardens

This beautifully landscaped 92-acre arboretum features woodland trails, a fernery, seasonal blooms, garden railway, Japanese Overlook and sculpture exhibits.

Meadow at Morris Arboretum

Phone: +1215‑247‑5777

Official site

 

Chestnut Hill Historic District (Brookline)

Explore grand late‑19th‑century homes in Colonial, Tudor, and Victorian styles lining tree‑shaded streets—perfect for history and architecture enthusiasts.

Chestnut Hill Historic District in Brookline

Phone: (no direct office)

More info

 

The Street at Chestnut Hill

An open-air retail and dining plaza with boutique shops, seasonal farmers markets, live performances, and outdoor seating for relaxed community vibes.

The Street at Chestnut Hill

Phone: +1617‑278‑1850

Official site

 

Showcase Cinema SuperLux

Enjoy the latest films in luxury recliners with full-service dining and cocktail delivery—perfect for a pampered movie night.

Chestnut Hill Mall area

Phone: +1617‑965‑9919

Official site

 

Longyear Museum – Mary Baker Eddy Historic House

Visit the beautifully restored 19th-century home of Christian Science founder Mary Baker Eddy, complete with period furnishings and guided interpretive tours.

Longyear Museum exterior

Phone: +1617‑278‑9000

Official site

 

Reginald A. Fessenden House

This National Historic Landmark honors radio pioneer Reginald Fessenden and showcases early-20th-century architecture right in a residential Chestnut Hill neighborhood.

Fessenden House exterior

Phone: (private property)

More info

 

Newton Centre Playground & Splash Pad

A family-friendly park featuring a modern playground and seasonal splash pad—perfect for kids to cool off during warm days.

Newton Centre Playground

Phone: (no direct office)

More info

 

Chestnut Hill Mall (RIP – Historic Site)

Former shopping mall site now undergoing redevelopment; still worth a quick stroll to appreciate late-20th-century commercial architecture and modern urban planning.

Chestnut Hill Mall exterior

Phone: (site under redevelopment)

More info

 

Alumni Stadium (Boston College)

Catch a Boston College Eagles football game in this spirited stadium set within a wooded Chestnut Hill campus—a great way to tap into local college culture.

Alumni Stadium

Phone: +1617‑552‑0124

Official site

 

Angier Woods Conservation Area

A peaceful glacial woodland trail offering dappled shade, fern-lined paths, and occasional deer sightings—perfect for hikers seeking local solitude.

Angier Woods trail

Phone: (no direct office)

Official site

 

Webster Conservation Area

Winding through hardwood forests and marshy ponds, these peaceful trails are ideal for birdwatching, meditative walks, and little outdoor escapes.

Webster Conservation trail

Phone: (no direct office)

Official site

 

Franklin Morton playground at Reservoir Park

A charming neighborhood playground adjacent to the reservoir, perfect for families seeking a shaded play area and picnic spots.

Reservoir Park playground

Phone: (no direct office)

More info

 

Chestnut Hill Branch – Boston Public Library

A cozy neighborhood library branch offering a mix of books, community events, and quiet reading areas in a welcoming local atmosphere.

Chestnut Hill Library

Phone: +1617‑566‑8410

Official site

 

Skywalk Observatory – Prudential Center*

Just a short drive away, enjoy panoramic Boston city views from the 50th floor—ideal at sunset or dusk for expansive skyline panoramas.

Prudential Tower

Phone: +1617‑536‑8753

Official site

 

Chestnut Hill Dog Park

A fenced-in, off-leash dog park where local pet owners gather—great for socializing both dogs and humans on a sunny afternoon.

Dog park in Boston area

Phone: (no direct office)

More info

 

Brookline Reservoir Park

A scenic greenspace with benches and open lawns adjacent to the reservoir—great spot for reading, relaxing, or casual weekend picnics.

Brookline Reservoir Park

Phone: (no direct office)

More info

 

Beacon Street Trolley Ride (Seasonal)

Take a nostalgic ride on a historic streetcar during warmer months—a charming way to experience local culture and vintage transit history.

Historic Boston trolley

Phone: (operated by MBTA)

Official site

 

Warehouse Restaurant & Tap Room

A lively gastropub housed in a restored brick building, offering craft beers, elevated pub fare, and a cozy, communal atmosphere.

Warehouse Restaurant exterior

Phone: +1617‑232‑6020

Official site

 

Studio Parco Pottery & Art Studios

Join a hands-on pottery or art class at this charming local studio—perfect for creatives or families seeking an engaging experience.

Pottery studio wheel

Phone: +1617‑738‑2550

Official site

 

Putterham Meadows & Golf Course

An 18‑hole public golf course with tree-lined fairways and a scenic setting—suitable for beginners and seasoned golfers alike.

Putterham Meadows golf course

Phone: +1617‑730‑2322

More info

 

Otis Wildlife Sanctuary

A designated wildlife preserve featuring tidal flats, salt marshes, and boardwalks—brilliant for birdwatching and coastal ecology enthusiasts.

Wetlands boardwalk

Phone: (no direct office)

Official site

 

Brookline Booksmith

A beloved independent bookstore with a vast selection of new titles, regular author readings, and a warm community vibe just minutes from Chestnut Hill.

Brookline Booksmith storefront

Phone: +1617‑566‑6660

Official site

 

Newton Farmer’s Market (Seasonal)

Local producers gather at the Brookline Reservoir area on weekends to offer fresh farm goods, baked treats, artisan crafts, and live music.

Boston farmers market stalls

Phone: (seasonal info via City of Newton)

More info

 

Graffiti Alley (Brookline)

A small, unofficial alley filled with ever-changing street art—a colorful, urban canvas loved by local creatives and photographers.

Colorful urban street art

Phone: (no direct office)

More info

 

Lunch at Volturno Wine Bar & Trattoria

Enjoy modern Italian cuisine in a cozy setting with wood-fired pizzas and locally sourced ingredients—perfect for a relaxed midday meal.

Italian trattoria interior

Phone: +1617‑277‑5155

Official site

 

Chestnut Hill Mall Gardens

Seasonal garden displays and fountain features set in an open plaza—ideal for a short, relaxing pause during shopping or dining outings.

Mall gardens and fountain

Phone: (mall management)

More info

 

Walk the Muddy River Pathway

A scenic walking route following the Muddy River through Olmsted-designed parkland—tranquil, tree-lined, with occasional wildlife sightings.

Muddy River pathway

Phone: (no direct office)

More info

 

Yoga in the Park (Seasonal Pop-up)

Join free or low-cost outdoor yoga classes near the reservoir during summer—great way to stretch, relax, and meet locals in a peaceful environment.

Outdoor yoga class

Phone: (check local listings)

More info

 

Norumbega Park Site

Once a beloved late-19th‑century amusement park, this landscaped spot now offers walking paths, picnic areas, and a touch of local nostalgia near the reservoir.

Vintage Norumbega Park illustration

Phone: (historical site)

Learn more

 

Boston Marathon Finishing Stretch (Beacon St.)

Watch runners conquer the final leg of the iconic Boston Marathon as they traverse Beacon Street through Chestnut Hill—a warm and inspiring community spectacle.

Boston Marathon finishers

Phone: (event-based)

Official site

 

Chestnut Hill Spanish River Parks

A series of small urban green spaces with seating, flowering shrubs, and benches—perfect spots for relaxation between shops or after walks.

Small urban park path

Phone: (no direct office)

More info

 

Masonic Headquarters (Evergreen Lodge)

Historic Masonic lodge building featuring early-20th-century architecture; while not open daily, it's an intriguing exterior for architecture enthusiasts.

Historic lodge building

Phone: (private)

Learn more

 

Parker’s Restaurant & Bar

A neighborhood favorite offering elevated American comfort food in a polished setting—great for brunch or evening gatherings.

Restaurant interior

Phone: +1617‑232‑9500

Official site

 

Claflin Building (BC Campus)

This stately academic building houses lecture halls and reading rooms—its elegant façade is great for campus photos or a quiet moment outdoors.

Claflin Hall at Boston College

Phone: +1617‑552‑8000

Official site

 

Chestnut Hill Music Corner

A cozy music shop offering instrument sales, repairs, and rentals—ideal for music lovers or anyone in need of musical gear.

Music store front

Phone: +1617‑738‑4412

Official site

 

Elliot Street Allée

A tree-lined formal walkway connecting residential streets to the campus mall—perfect for a quiet, shaded stroll in the neighborhood.

Tree-lined neighborhood path

Phone: (no direct office)

More info

 

Café Dream Boston

A charming café serving coffee, pastries, and light meals—great spot to relax between activities or meet before exploring.

Cozy café interior

Phone: +1617‑731‑9699

Official site

 

Shaw’s Supermarket

A convenient local grocery store perfect for picking up supplies—great for families and travelers staying nearby.

Supermarket entrance

Phone: +1617‑277‑4880

Official site

 

Chestnut Hill Chapel

A charming small chapel built in the early 20th century, featuring graceful architecture and stained-glass windows visible from the exterior.

Historic chapel building

Phone: (no public office)

More info

 

Walk the Lower Falls Parkway

Stroll or cycle along this scenic road beside the Charles River, offering lush landscaping and peaceful neighborhood views just a bit further afield.

Riverside pathway

Phone: (no direct office)

More info

 

Seasonal Ice Skating at Larz Anderson Park*

Head to this nearby Brookline park in winter for public ice skating on a charming pond—classic New England fun for families & couples alike.

Couple skating outdoors

Phone: +1617‑730‑2080

More info

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