Outbound Collective logo

Top Spots

Hike at Haystack Mountain State Park

Litchfield County, Connecticut

4.0
1.78 mi / 226 ft gain

Hike Dennis Hill Gazebo Loop Trail

Litchfield County, Connecticut

1.8 mi / 180 ft gain

Hike Pine Mountain And Eastern Summit

Litchfield County, Connecticut

4.7 mi / 610 ft gain

Hike to Campbell Falls

Norfolk, Connecticut

4.0
1.4 mi / 187 ft gain

Hike Stone Man Mountain Via Iron Trail

Canaan, Connecticut

2.7 mi / 672 ft gain

Hike Iron Trail

North Canaan, Connecticut

7.6 mi / 1 ft gain

Hike Goshen Land Trust Trail

Goshen, Connecticut

2 mi / 347 ft gain

Bartholomew's Cobble Trail

Sheffield, Massachusetts

3.6 mi / 666 ft gain

Hike Appalachian Trail: Falls Village To West Cornwall Road

Canaan, Connecticut

18.2 mi / 3 ft gain

Places to stay

Echo Hill

New Marlborough, Massachusetts

Echo Hill

From $150 / night

Meadow Ridge Farm Woods

Litchfield, Connecticut

Meadow Ridge Farm Woods

From $135 / night

Maple Corner Farm's Meadow Site

Maple Corner Farm's Meadow Site

From $120 / night

Meadow Ridge Farm   Meadow

Litchfield, Connecticut

Meadow Ridge Farm Meadow

From $145 / 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

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

Quick links