The Top 20 Attractions around Winchester
There are plenty of places to see and visit around Winchester. Whether you love hiking or cycling, Winchester is a region where 20
hidden gems are waiting to be explored and visited. Check the top places to visit in the region and plan your next adventure today.
hidden gems are waiting to be explored and visited. Check the top places to visit in the region and plan your next adventure today.
Last updated: October 22, 2025
Minuteman Bikeway
Highlight (Segment) • Cycleway
The Minuteman Bikeway is a 10-mile paved rail-trail in Greater Boston, which follows the historic path of the 1775 American Revolution's beginnings. Stretching from Bedford to the Alewife Station in …
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U.S.S. Constitution
Highlight • Historical Site
Frigate of the United States Navy and the oldest seaworthy warship in the world and second oldest still in service after HMS Victory. One, if not the symbol of America's …
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Bunker Hill Monument
Highlight • Monument
The Bunker Hill Monument in Boston commemorates the Battle of Bunker Hill during the American Revolution. Standing at 221 feet, it offers panoramic views of the city. Completed in 1843, …
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Lexington Battle Green
Highlight • Historical Site
The Lexington Battle Green, also known as Lexington Common, is a historic site in Lexington, Massachusetts. On April 19, 1775, this green was the site of the first armed conflict …
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Winthrop Square
Highlight • Historical Site
Winthrop Square, near Bunker Hill, holds a storied past dating back to the colonial era. Named after John Winthrop, Massachusetts Bay Colony's inaugural governor, the square served as a vital …
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