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Rutland

Best Hiking Trails near Rutland, Massachusetts

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Overview

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

  • Hiking Trails (1,059)
  • Parks & Forests (29)
  1. 1
    Hancock Hill via North Skyline Trail
    ★ ★ ★ ★ ★ EASY 2.9 mi
  2. 2
    Mount Watatic Loop via Wapack Trail
    ★ ★ ★ ★ ★ EASY 4.1 mi
  3. 3
    Beauregard Lot via Half Way House Road
    ★ ★ ★ ★ ★ MODERATE 5.0 mi
  4. 4
    Horse Caves Loop via NET/M&M Trail and Robert Frost Trail
    ★ ★ ★ ★ ★ EASY 3.4 mi
  5. 5
    Great Blue Hill via Summit Road
    ★ ★ ★ ★ ★ EASY 2.0 mi
  6. 6
    Beauregard Lot via Dublin Trail / Monadnock-Sunapee Greenway
    ★ ★ ★ ★ ★ MODERATE 4.3 mi
  7. 7
    Sawyer Lot Loop via White Dot Trail
    ★ ★ ★ ★ ★ MODERATE 5.4 mi
  8. 8
    A hike through Mt. Holyoke Range and Skinner State Parks
    ★ ★ ★ ★ ★ MODERATE 7.4 mi
  9. 9
    Pack Monadnock Mountain via Raymond Trail
    ★ ★ ★ ★ ★ EASY 2.8 mi
  10. 10
    Breakneck Ledge Loop via North Skyline Trail
    ★ ★ ★ ★ ★ EASY 3.5 mi

Green Mountain National Forest
Green Mountain National Forest
Douglas State Forest
Borderland State Park
Freetown-Fall River State Forest
Douglas State Forest
Boston Harbor Islands National Recreation Area
Great Meadows National Wildlife Refuge
Bigelow Hollow State Park
Blackstone River and Canal Heritage State Park
Erving State Forest
Farmington Canal Line State Park Trail
Federated Women's Club State Forest
Great Meadows National Wildlife Refuge
Great Meadows National Wildlife Refuge
Colt State Park
Airline State Park Trail (Northern Section)
Airline State Park Trail (Southern Section)
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
Enders State Forest
Fall River Heritage State Park
Roger Williams National Monument
Airline State Park Trail (Northern Section)