Outbound Collective logo

Top Spots

Mount Tom and Deadtop via Whiting Reservoir Road

Holyoke, Massachusetts

5.82 mi / 1070 ft gain

Mount Tom via Metacomet-Monadnock Trail (Short Option)

Holyoke, Massachusetts

2.17 mi / 584 ft gain

Ashley Reservoir Trail

Holyoke, Massachusetts

3.48 mi / 138 ft gain

Dinosaur Footprints Trail

Holyoke, Massachusetts

0.26 mi / 36 ft gain

Whiting Street Reservoir Loop

Holyoke, Massachusetts

3.74 mi / 138 ft gain

Mount Tom

Holyoke, Massachusetts

1.26 mi / 561 ft gain

Mount Tom Traverse via Metacomet-Monadnock Trail

Holyoke, Massachusetts

5.12 mi / 1030 ft gain

T. Bagg, NET/MM and Keystone Trail Loop

Holyoke, Massachusetts

5.31 mi / 1033 ft gain

Mount Tom via Quarry Trail

Holyoke, Massachusetts

3.76 mi / 518 ft gain

Places to stay

Northampton / Springfield KOA Holiday

Westhampton, Massachusetts

Northampton / Springfield KOA Holiday

Indian Hollow

Chesterfield, Massachusetts

Indian Hollow

Westville Recreation Area

Sturbridge, Massachusetts

Westville Recreation Area

Tully Lake Recreation Area (Ma)

Athol, Massachusetts

Tully Lake Recreation Area (Ma)

Buffumville Lake (Group Shelters)

Charlton, Massachusetts

Buffumville Lake (Group Shelters)

West Thompson Lake Campground

Thompson, Connecticut

West Thompson Lake Campground

Guides and stories

Escape to These 8 Private Campsites in Massachusetts’ Berkshire Mountains

Escape to These 8 Private Campsites in Massachusetts’ Berkshire Mountains

The Outbound Collective

 5 Tips for Finding Beautiful Fall Foliage in Massachusetts

5 Tips for Finding Beautiful Fall Foliage in Massachusetts

Gustavo Quiros

Quick links