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Best trails in Winthrop

186 Reviews
Explore the most popular trails near Winthrop with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers and nature lovers like you.
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Map of trails in Winthrop
Top trails (2)
#1 - Deer Island Trail
Boston Harbor Islands National Recreation Area
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(128)
Length: 2.7 mi • Est. 1 h 8 m
This path is paved with very little change in elevation. The path offers stunning views of the ocean, of Winthrop, and of the nearby islands. Accessibility: The trail surface is paved and typically at least five feet wide. The grade is mostly gentle (all estimated 5% or less) so most wheelchair and stroller users will likely find the trail navigable.Show more
#2 - Georges Island
Boston Harbor Islands National Recreation Area
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(3)
Length: 0.9 mi • Est. 25 m
This is a beautiful historic island that is accessible via ferry during the summer. The island plays host to Fort Warren, an interesting relic of the American Civil War.Show more