Top Spots

Hike Sharon Audubon Center Loop

Sharon, Connecticut

1.6 mi / 114 ft gain

Hike Pine Knob Via Appalachian Trail Loop

Sharon, Connecticut

2.6 mi / 770 ft gain

Hike the Pine Knob Loop, Housatonic Meadows SP

Sharon, Connecticut

5.0
2.5 mi / 770 ft gain

Hike Housatonic River Via Appalachian Trail

Sharon, Connecticut

10.4 mi / 1 ft gain

Hike Sharon Mountain Via Appalachian Trail

Salisbury, Connecticut

4.7 mi / 1 ft gain

Hike Cathedral Pines And Mohawk Mountain Trail

Cornwall, Connecticut

5.4 mi / 1 ft gain

Hike Macedonia Brook Loop

Kent, Connecticut

6.8 mi / 1 ft gain

Explore Kent Falls

Kent, Connecticut

5.0
0.75 mi / 250 ft gain

Hike Kent Falls Via Appalachian Trail

Kent, Connecticut

6.7 mi / 147 ft gain

Places to stay

Millerton, New York

Driftways Farm

From $125 / night

Pine Plains, New York

Hudson Valley Hilltop 2

From $169 / night

Pine Plains, New York

Hudson Valley Hilltop 1

From $169 / night

Litchfield, Connecticut

Meadow Ridge Farm Woods

From $135 / night

Litchfield, Connecticut

Meadow Ridge Farm Meadow

From $145 / night

Stanfordville, New York

A Riverwalk

From $125 / night

Guides and stories

Escape to These 8 Private Campsites in Massachusetts’ Berkshire Mountains

The Outbound Collective

Pursuit Gear Kit 2018

Pursuit Series

Trading the Metro for the Mountains: Pursuit New York 2018

Emily Hlaváč Green

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

Chasing Fall: A Day in the Catskills

Jack Tumen

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