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Best Hiking Trails near Winthrop, Massachusetts

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Overview

Explore hiking trails around Winthrop, Massachusetts. The best hike near Winthrop is Hancock Hill via North Skyline Trail, a 2.9 mile oneway in .

  • Hiking Trails (646)
  • Parks & Forests (22)
  1. 1
    Hancock Hill via North Skyline Trail
    ★ ★ ★ ★ ★ EASY 2.9 mi
  2. 2
    Great Blue Hill via Summit Road
    ★ ★ ★ ★ ★ EASY 2.0 mi
  3. 3
    Breakneck Ledge Loop via North Skyline Trail
    ★ ★ ★ ★ ★ EASY 3.5 mi
  4. 4
    Babson Farms Quarry
    ★ ★ ★ ★ ★ EASY 1.4 mi
  5. 5
    Lake Cochichewick Loop via Edgewood Farm Trail and Stevens Trail
    ★ ★ ★ ★ ★ EASY 2.5 mi
  6. 6
    Puds Pond Loop via Pond Walk
    ★ ★ ★ ★ ★ EASY 2.9 mi
  7. 7
    Wachusett Mountain Loop via Bicentennial Trail
    ★ ★ ★ ★ ★ EASY 1.7 mi
  8. 8
    Melrose Rock Loop via Rock Circuit Trail
    ★ ★ ★ ★ ★ EASY 4.5 mi
  9. 9
    Quarry Spring Loop via Quarry Road and Skyline Trail
    ★ ★ ★ EASY 1.2 mi
  10. 10
    Bellevue Pond via Skyline Trail
    ★ ★ ★ ★ ★ EASY 1.3 mi

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