Top Spots

Hike Appalachian Trail: Mount Algo To Bull's Bridge

Kent, Connecticut

6.9 mi / 1 ft gain

Hike Caleb Peak Via Appalachian Trail

Kent, Connecticut

8.9 mi / 2 ft gain

Hike River Road

Kent, Connecticut

2.7 mi / 114 ft gain

Hike Appalachian Trail: Algo Shelter To Pine Swamp Shelter

Kent, Connecticut

14.3 mi / 2 ft gain

Hike Appalachian Trail: St. Johns Ledges To Glacier Rock

Kent, Connecticut

8.6 mi / 2 ft gain

Hike the Ridge Loop Trail, Macedonia Brook SP

Kent, Connecticut

3.0

Hike Cobble Mountain

Kent, Connecticut

2.2 mi / 695 ft gain

Schaghticoke Mountain via Appalachian Trail

Kent, Connecticut

2.97 mi / 984 ft gain

Hike Kent Falls Via Appalachian Trail

Kent, Connecticut

6.7 mi / 147 ft gain

Places to stay

Litchfield, Connecticut

Meadow Ridge Farm Meadow

From $145 / night

Litchfield, Connecticut

Meadow Ridge Farm Woods

From $135 / night

Millerton, New York

Driftways Farm

From $125 / night

Clinton Corners, New York

Creekside Solitude

From $75 / night

Pine Plains, New York

Hudson Valley Hilltop 2

From $169 / night

Stanfordville, New York

A Riverwalk

From $125 / night

Guides and stories

5 Reasons to Plan a Summer Getaway to Bear Mountain, New York

Sara Sheehy

Escape the Bustle of New York City with a Weekend at Bear Mountain

The Outbound Collective

Earth Day 2020 Goes Online: How to Get Involved

Jonathan Stull

Escape to These 8 Private Campsites in Massachusetts’ Berkshire Mountains

The Outbound Collective

Pursuit Gear Kit 2018

Pursuit Series

Quick links