Winthrop Square · Best Landmarks · Curated · Updated 2026

Best Landmarks near Winthrop Square

Discover the best landmarks near Winthrop Square. Find inspiration for your trip with our curated list of top-rated spots, local favorites, and hidden gems.

The 10 best landmarks near Winthrop Square

alaska/alaska-peninsula/landmark/john-fitzgerald-kennedy-national-historic-site

John Fitzgerald Kennedy National Historic Site

Discover the roots of JFK at his birthplace in Brookline, MA. Explore the home where a future president's journey began.

83 Beals St, Brookline, MA 02446
4.6 Excellent 350 reviews
massachusetts/boston/fenway-kenmore/landmark/ramler-park

Ramler Park

Discover the tranquil beauty of Ramler Park in Boston's Fenway-Kenmore neighborhood, perfect for relaxation and outdoor activities.

130 Peterborough St, Boston, MA 02215
4.6 Excellent 102 reviews
massachusetts/boston/fenway-kenmore/landmark/the-green-monster

The Green Monster

Experience the thrill of baseball at The Green Monster in Fenway Park, where history and excitement collide in the heart of Boston.

4 Jersey St, Boston, MA 02215
5 Excellent 17 reviews
massachusetts/boston/fenway-kenmore/landmark/kenmore-square

Kenmore Square

Experience the vibrant energy of Kenmore Square in Boston, where iconic landmarks and cultural attractions come together in a lively plaza.

School of Education, 623 Commonwealth Ave, Boston, MA 02215
4.4 Very Good 694 reviews
massachusetts/boston/landmark/fenway-park

Fenway Park

Discover the historic Fenway Park, home to the Boston Red Sox, and immerse yourself in America's favorite pastime in a vibrant and iconic setting.

4 Jersey St, Boston, MA 02215
4.8 Excellent 38,271 reviews
massachusetts/boston/fenway-kenmore/landmark/klr

KLR

Explore KLR, a historical landmark in Boston's Fenway-Kenmore district, and immerse yourself in the city's rich heritage and stunning architecture.

Lansdowne St, Boston, MA 02215
massachusetts/boston/fenway-kenmore/landmark/citgo-sign

CITGO Sign

Discover the CITGO Sign, an iconic symbol of Boston's skyline located in lively Kenmore Square, perfect for photos and local exploration.

660 Beacon St, Boston, MA 02215
4.6 Excellent 25 reviews
massachusetts/boston/landmark/back-bay-fens

Back Bay Fens

Explore Back Bay Fens, a serene urban park in Boston, featuring beautiful landscapes, historic monuments, and vibrant gardens for a perfect outdoor experience.

100 Park Dr, Boston, MA 02215
4.5 Excellent 959 reviews
massachusetts/boston/fenway-kenmore/landmark/japanese-bell

Japanese Bell

Discover serenity at the Japanese Bell in Boston, a historical landmark symbolizing friendship between the U.S. and Japan amidst beautiful gardens.

Boston, MA 02215
4.6 Excellent 5 reviews
massachusetts/boston/fenway-kenmore/landmark/the-fenway-garden-society

The Fenway Garden Society

Explore Boston's hidden green gem at Fenway Victory Gardens, a serene community garden where nature and tranquility come together amidst the city's vibrancy.

1200 Boylston St, Boston, MA 02215
4.6 Excellent 219 reviews

More to explore near Winthrop Square

Jump into the most useful discovery pages nearby, from experiences and heritage highlights to food, stays, shopping, and evening ideas.

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More about Winthrop Square

Experience the tranquil beauty of Winthrop Square in Brookline, a perfect urban oasis with lush gardens and serene walking paths.

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