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Westport

Best Hiking Trails near Westport, Massachusetts

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Overview

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

  • Hiking Trails (303)
  • Parks & Forests (23)
  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
    Puds Pond Loop via Pond Walk
    ★ ★ ★ ★ ★ EASY 2.9 mi
  5. 5
    Boyce Hill Loop via Tucker Hill Path and Dark Hollow Path
    ★ ★ ★ ★ ★ MODERATE 5.7 mi
  6. 6
    Hancock Hill Loop via North Skyline Trail
    ★ ★ ★ ★ ★ EASY 3.5 mi
  7. 7
    Tucker Hill Loop
    ★ ★ ★ ★ ★ MODERATE 6.6 mi
  8. 8
    Easy 1.9 mi:Trailside Museum via Summit Rd/N Skyline Trail
    ★ ★ ★ ★ EASY 1.9 mi
  9. 9
    Flagstaff Hill
    ★ ★ ★ MODERATE 6.8 mi
  10. 10
    Breeze Hill Loop
    ★ ★ ★ ★ DIFFICULT 9.6 mi

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