Outbound Collective logo

Top Spots

Dover Stone Church

Dover Plains, New York

3.64 mi / 768 ft gain

Hike Dover's Stone Church

Dover Plains, New York

4.5

Hike Caleb Peak Via Appalachian Trail

Kent, Connecticut

8.9 mi / 2 ft gain

Hike Appalachian Trail: Mount Algo To Bull's Bridge

Kent, Connecticut

6.9 mi / 1 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

Hike Macedonia Brook Loop

Kent, Connecticut

6.8 mi / 1 ft gain

Schaghticoke Mountain via Appalachian Trail

Kent, Connecticut

2.97 mi / 984 ft gain

Appalachian Trail: Bull's Bridge to Ten Mile Hill

Kent, Connecticut

4.55 mi / 1129 ft gain

Places to stay

Northfield Brook Lake Group Shelters

Thomaston, Connecticut

Northfield Brook Lake Group Shelters

Hop Brook Lake Recreation Area

Naugatuck, Connecticut

Hop Brook Lake Recreation Area

Getaway Catskills East

Catskill, New York

Getaway Catskills East

From $209 / night

Getaway Catskills West

Catskill, New York

Getaway Catskills West

From $209 / night

Bear Mountain Inn

Tomkins Cove, New York

Bear Mountain Inn

From $109 / night

Guides and stories

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

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

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

Earth Day 2020 Goes Online: How to Get Involved

Jonathan Stull

Escape to These 8 Private Campsites in Massachusetts’ Berkshire Mountains

Escape to These 8 Private Campsites in Massachusetts’ Berkshire Mountains

The Outbound Collective

Pursuit Gear Kit 2018

Pursuit Gear Kit 2018

Pursuit Series

Quick links