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Deer Island Harborwalk Loop
Waterfront loop with harbor vistas and skyline views.
Make a Day Trip
Estimated total time: Varies
Castle Island Harborwalk Trail
Coastal promenade walk with harbor and historic fort scenery.
Mount Everett Trail MA
Taconic ridge climb with broad summit views and rugged footing.
Blue Hills Skyline Trail
Traprock ridge route with expansive Greater Boston views.
About This Trail
A 2.7-mile paved waterfront loop circling Deer Island in Winthrop with sweeping views of downtown Boston, the Harbor Islands, and the open Atlantic. The Hillside Trail climbs to the park’s highest vantage point for panoramic skyline views, making this an easy and scenic coastal walk year-round.
Getting There
Nearby Trails
Castle Island Harborwalk Trail
Coastal promenade walk with harbor and historic fort scenery.
Mount Everett Trail MA
Taconic ridge climb with broad summit views and rugged footing.
Blue Hills Skyline Trail
Traprock ridge route with expansive Greater Boston views.
Revere Beach Reservation Walk
Flat shoreline route with ocean and city views.
Stony Brook Reservation Boundary Trail
Urban forest trail with mixed terrain and woodland canopy.
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