Top Spots

Kilburn Loop

Hinsdale, New Hampshire

6.14 mi / 712 ft gain

Mount Pisgah

Hinsdale, New Hampshire

4.82 mi / 679 ft gain

Chestnut Hill, Reservoir, and North Ponds Trail Loop

Hinsdale, New Hampshire

5.01 mi / 699 ft gain

Wantastiquet Natural Area Summit Trail

Hinsdale, New Hampshire

3.84 mi / 1020 ft gain

Stone Post Viewpoint and Indian Pond Lookout

Hinsdale, New Hampshire

5.8 mi / 1414 ft gain

Ann Stokes Loop and Daniels Mountain Loop

Chesterfield, New Hampshire

3.92 mi / 735 ft gain

Ann Stokes Loop

Chesterfield, New Hampshire

2.31 mi / 436 ft gain

Daniels Mountain via Ann Stokes

Chesterfield, New Hampshire

2.48 mi / 538 ft gain

Ann Stokes Trail to Indian Pond

Chesterfield, New Hampshire

1.28 mi / 243 ft gain

Places to stay

Hillside Camp

From $100 / night

Athol, Massachusetts

Tully Lake Recreation Area (Ma)

Surry, New Hampshire

Surry Mountain Lake Beach

Keene, New Hampshire

Otter Brook Lake Beach

Townshend, Vermont

Townshend Lake Day Use Area

Guides and stories

From NYC to the Slopes: A Weekend Ski Getaway

Sara Sheehy

5 Tips for Finding Beautiful Fall Foliage in Massachusetts

Gustavo Quiros

Escape to These 8 Private Campsites in Massachusetts’ Berkshire Mountains

The Outbound Collective

Quick links