Top Spots

Hike Raccoon Hill

Salisbury, Connecticut

3.2 mi / 570 ft gain

Hike Appalachian Trail: Salisbury To Jug End Road

Salisbury, Connecticut

15.6 mi / 4 ft gain

Hike Lions Head Via Appalachian Trail

Salisbury, Connecticut

4.4 mi / 1 ft gain

Hike Dark Hollow Loop

Salisbury, Connecticut

1.4 mi / 249 ft gain

Hike Lion's Head Peak Trail

Salisbury, Connecticut

2.5 mi / 613 ft gain

Hike Lion's Head Trail

Salisbury, Connecticut

4.1 mi / 885 ft gain

Hike Appalachian Trail: Lions Head To Bear Mountain

Salisbury, Connecticut

8.2 mi / 1 ft gain

Explore Riga Falls

Salisbury, Connecticut

Hike to Rand's View

Salisbury, Connecticut

5.3 mi / 1395 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

New Marlborough, Massachusetts

Echo Hill

From $150 / night

Hillsdale, New York

Hillsdale Hideaway

From $125 / night

MALOWINA FOREST

From $200 / 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

Chasing Fall: A Day in the Catskills

Jack Tumen

Quick links