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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 (978)
  • Parks & Forests (32)
  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
    Breakneck Ledge Loop via North Skyline Trail
    ★ ★ ★ ★ ★ EASY 3.5 mi
  9. 9
    Pack Monadnock Mountain via Raymond Trail
    ★ ★ ★ ★ ★ EASY 2.8 mi
  10. 10
    Beauregard Lot via Pumpelly Trail
    ★ ★ ★ ★ ★ MODERATE 4.0 mi

Green Mountain National Forest
Green Mountain National Forest
Lye Brook Wilderness
Douglas State Forest
Freetown-Fall River State Forest
Borderland State Park
Douglas State Forest
Great Meadows National Wildlife Refuge
American Legion State Forest
Gay City State Park
Bigelow Hollow State Park
Blackstone River and Canal Heritage State Park
Airline State Park Trail (Northern Section)
Erving State Forest
Federated Women's Club State Forest
Great Meadows National Wildlife Refuge
Great Meadows National Wildlife Refuge
Airline State Park Trail (Southern Section)
Farmington Canal Line State Park Trail
American Legion State Forest
Wilderness Lake Campground
Beaver Brook State Park
Bolton Notch State Park
Connecticut River Greenway State Park
Connecticut River Greenway State Park
Connecticut River Greenway State Park
Connecticut River Greenway State Park
Dinosaur State Park
Enders State Forest
Fall River Heritage State Park