Destination guide
More about Winthrop Square
Experience the tranquil beauty of Winthrop Square in Brookline, a perfect urban oasis with lush gardens and serene walking paths.
Tell me more about Winthrop Square
Winthrop Square · Best Attractions · Curated · Updated 2026
Best Attractions near Winthrop Square
Discover the best attractions near Winthrop Square. Find inspiration for your trip with our curated list of top-rated spots, local favorites, and hidden gems.
The 10 best attractions near Winthrop Square
Winthrop Square
Experience the tranquil beauty of Winthrop Square in Brookline, a perfect urban oasis with lush gardens and serene walking paths.
St Paul St & Freeman St, Brookline, MA 02445
John Fitzgerald Kennedy National Historic Site
Discover the early life of John F. Kennedy at his historic home, a captivating tribute in Brookline, Massachusetts, rich with history and insightful exhibits.
83 Beals St, Brookline, MA 02446
Audubon Circle
Explore the historic beauty of Audubon Circle in Boston, a serene landmark blending culture, leisure, and nature.
Audubon Circle, Boston, MA 02215
Boston University
Discover the historical and cultural richness of Boston University, a premier private university in the heart of Boston with stunning architecture and vibrant campus life.
Commonwealth Ave, Boston, MA 02215
Judson B. Coit Observatory
Explore the cosmos at Judson B. Coit Observatory in Boston, a captivating destination for stargazers and astronomy lovers alike.
685 Commonwealth Ave, Boston, MA 02215
Ramler Park
Explore Ramler Park, a beautiful urban oasis in Fenway-Kenmore, Boston, perfect for relaxation, picnics, and enjoying nature's beauty.
130 Peterborough St, Boston, MA 02215
Official Red Sox Team Store
Explore the Official Red Sox Team Store in Boston for unique memorabilia and fan gear, celebrating the legacy of one of baseball's most beloved teams.
19 Jersey St, Boston, MA 02215
The Green Monster
Discover The Green Monster at Fenway Park - a historic landmark and cultural icon in the heart of Boston, celebrating baseball and local heritage.
4 Jersey St, Boston, MA 02215
Kenmore Square
Discover the vibrant energy of Kenmore Square, Boston's iconic plaza, where history, dining, and entertainment come together in a lively setting.
School of Education, 623 Commonwealth Ave, Boston, MA 02215
Fenway Park
Explore the historic Fenway Park in Boston, a legendary baseball stadium that embodies the spirit of America's pastime.
4 Jersey St, Boston, MA 02215
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.
Get the app
Your all‑in‑one travel companion app
Explore expert travel guides, compare and book tours, experiences, hotels, and more—all from the palm of your hand. Download now for seamless trip planning wherever your wanderlust takes you.