Top Spots

Stissing Mountain Trail

Pine Plains, New York

1.8 mi / 866 ft gain

Stissing Mountain Full Loop

Stanfordville, New York

2.25 mi / 236 ft gain

Explore Wethersfield Estate & Gardens

Stanfordville, New York

Round Ball Mountain Trail

Ancram, New York

3.58 mi / 666 ft gain

Overmountain Conservation Area Trail

Ancram, New York

3.11 mi / 295 ft gain

Iron Mine Pond Loop

Millerton, New York

4.36 mi / 725 ft gain

Brace Mountain Trail

Millerton, New York

3.68 mi / 1450 ft gain

Explore Riga Falls

Salisbury, Connecticut

Mount Frissell and Brace Mountain Loop Trail

Mount Washington, Massachusetts

5.08 mi / 807 ft gain

Places to stay

Red Hook, New York

Vista Valley wooded pond Sites 2

From $150 / night

Pine Plains, New York

Hudson Valley Hilltop 1

From $169 / night

Red Hook, New York

Private Peaceful Farm Venture

From $99 / night

Pine Plains, New York

Hudson Valley Hilltop 2

From $169 / night

Hucklebuck Railway Camp East

From $140 / night

Millerton, New York

Driftways Farm

From $125 / night

Guides and stories

Pursuit Gear Kit 2018

Pursuit Series

Trading the Metro for the Mountains: Pursuit New York 2018

Emily Hlaváč Green

Escape to These 8 Private Campsites in Massachusetts’ Berkshire Mountains

The Outbound Collective

Chasing Fall: A Day in the Catskills

Jack Tumen

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

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