Outbound Collective logo

Top Spots

Hike Iron Trail

North Canaan, Connecticut

7.6 mi / 1 ft gain

Bartholomew's Cobble Trail

Sheffield, Massachusetts

3.6 mi / 666 ft gain

Hike Stone Man Mountain Via Iron Trail

Canaan, Connecticut

2.7 mi / 672 ft gain

Hike to Rand's View

Salisbury, Connecticut

5.3 mi / 1395 ft gain

Hike Mount Prospect And Raccoon Hill Via Appalachian Trail

Salisbury, Connecticut

6.3 mi / 1 ft gain

Explore Great Falls

Canaan, Connecticut

3.0
0.5 mi

Hike Appalachian Trail: Bear Mountain To Race Brook Falls

Salisbury, Connecticut

9.2 mi / 2 ft gain

Bear Mountain Loop

Salisbury, Connecticut

5.0
6.05 mi / 1516 ft gain

Hike Raccoon Hill

Salisbury, Connecticut

3.2 mi / 570 ft gain

Places to stay

Echo Hill

New Marlborough, Massachusetts

Echo Hill

From $150 / night

Hillsdale Hideaway

Hillsdale, New York

Hillsdale Hideaway

From $125 / night

Driftways Farm

Millerton, New York

Driftways Farm

From $125 / night

Hudson Valley Hilltop 2

Pine Plains, New York

Hudson Valley Hilltop 2

From $169 / night

Hudson Valley Hilltop 1

Pine Plains, New York

Hudson Valley Hilltop 1

From $169 / night

Meadow Ridge Farm Woods

Litchfield, Connecticut

Meadow Ridge Farm Woods

From $135 / night

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