Outbound Collective logo

Top Spots

Appalachian Trail: Monterey to Sheffield

Sheffield, Massachusetts

7.19 mi / 1365 ft gain

Mount Everett - South Pinnacle

Sheffield, Massachusetts

1.82 mi / 1086 ft gain

East Mountain via Appalachian Trail

Great Barrington, Massachusetts

9.25 mi / 1857 ft gain

Hike to Race Brook Falls

Sheffield, Massachusetts

4.0
3.4 mi / 1174 ft gain

Race Brook Trail to Mount Race

Sheffield, Massachusetts

5.51 mi / 1663 ft gain

Race Brook Falls and Mount Everett

Sheffield, Massachusetts

6.31 mi / 2156 ft gain

Bartholomew's Cobble Trail

Sheffield, Massachusetts

3.6 mi / 666 ft gain

Appalachian Trail from Jug End to Bear Mountain

Egremont, Massachusetts

10.81 mi / 3074 ft gain

Hike Mount Everett

Mount Washington, Massachusetts

4.6 mi

Places to stay

Getaway Catskills East

Catskill, New York

Getaway Catskills East

From $209 / night

Getaway Catskills West

Catskill, New York

Getaway Catskills West

From $209 / night

Indian Hollow

Chesterfield, Massachusetts

Indian Hollow

Northampton / Springfield KOA Holiday

Westhampton, Massachusetts

Northampton / Springfield KOA Holiday

Northfield Brook Lake Group Shelters

Thomaston, Connecticut

Northfield Brook Lake Group Shelters

Hop Brook Lake Recreation Area

Naugatuck, Connecticut

Hop Brook Lake Recreation Area

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

Pursuit Gear Kit 2018

Pursuit Gear Kit 2018

Pursuit Series

Trading the Metro for the Mountains: Pursuit New York 2018

Trading the Metro for the Mountains: Pursuit New York 2018

Emily Hlaváč Green

Quick links