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Oakham

Best Hiking Trails near Oakham, Massachusetts

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Overview

Explore hiking trails around Oakham, Massachusetts. The best hike near Oakham is Mount Watatic Loop via Wapack Trail, a 4.1 mile loop in Mount Watatic Reservation.

  • Hiking Trails (760)
  • Parks & Forests (19)
  1. 1
    Mount Watatic Loop via Wapack Trail
    ★ ★ ★ ★ ★ EASY 4.1 mi
  2. 2
    Beauregard Lot via Half Way House Road
    ★ ★ ★ ★ ★ MODERATE 5.0 mi
  3. 3
    Horse Caves Loop via NET/M&M Trail and Robert Frost Trail
    ★ ★ ★ ★ ★ EASY 3.4 mi
  4. 4
    Great Blue Hill via Summit Road
    ★ ★ ★ ★ ★ EASY 2.0 mi
  5. 5
    Beauregard Lot via Dublin Trail / Monadnock-Sunapee Greenway
    ★ ★ ★ ★ ★ MODERATE 4.3 mi
  6. 6
    A hike through Mt. Holyoke Range and Skinner State Parks
    ★ ★ ★ ★ ★ MODERATE 7.4 mi
  7. 7
    Sawyer Lot Loop via White Dot Trail
    ★ ★ ★ ★ ★ MODERATE 5.4 mi
  8. 8
    Pack Monadnock Mountain via Raymond Trail
    ★ ★ ★ ★ ★ EASY 2.8 mi
  9. 9
    Breakneck Ledge Loop via North Skyline Trail
    ★ ★ ★ ★ ★ EASY 3.5 mi
  10. 10
    Mt Monadnock State Park Campground via Birchtoft Trail
    ★ ★ ★ ★ ★ MODERATE 6.6 mi

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