Top Spots

Rock via Old Pine Nook Road

Deerfield, Massachusetts

1.32 mi / 259 ft gain

Canalside Rail Trail

Montague, Massachusetts

7.23 mi / 223 ft gain

Mohawk Trail Scenic Drive

Greenfield, Massachusetts

34.61 mi / 2864 ft gain

North Sugarloaf via Brookside and Pocumtuck Ridge Trail

Deerfield, Massachusetts

2.93 mi / 594 ft gain

Temple Woods Loop Trail

Greenfield, Massachusetts

2.84 mi / 299 ft gain

Sachem Head

Greenfield, Massachusetts

1.82 mi / 59 ft gain

Sunderland Caves and Sugar Shack via Robert Frost Trail

Sunderland, Massachusetts

2.42 mi / 446 ft gain

Mount Toby via Sugar Farms to Summit to Tower Loop

Sunderland, Massachusetts

5.96 mi / 1037 ft gain

Mount Toby via Robert Frost Trail

Sunderland, Massachusetts

3.08 mi / 948 ft gain

Places to stay

Camp Cozie Nook

From $70 / night

Living Water Campsites: Mossy Acres 1

From $99 / night

Living Water Campsites: Mossy Acres 2

From $99 / night

Chesterfield, Massachusetts

Indian Hollow

Westhampton, Massachusetts

Northampton / Springfield KOA Holiday

Worthington, Massachusetts

Tamarack at Running Fox Berry Farm

From $115 / night

Guides and stories

5 Tips for Finding Beautiful Fall Foliage in Massachusetts

Gustavo Quiros

Escape to These 8 Private Campsites in Massachusetts’ Berkshire Mountains

The Outbound Collective

From NYC to the Slopes: A Weekend Ski Getaway

Sara Sheehy

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