Outbound Collective logo

Top Spots

Hike Housatonic River Trail

New Milford, Connecticut

10.1 mi / 413 ft gain

Hike River Road Pond Loop

New Milford, Connecticut

2.7 mi / 183 ft gain

Pawling Nature Preserve Red Trail

Pawling, New York

5.69 mi / 351 ft gain

Hike Appalachian Trail: Hoyt Road To Bull's Bridge

Sherman, Connecticut

7.9 mi / 1 ft gain

Hike Pine Hill Road Loop

New Fairfield, Connecticut

1.9 mi / 291 ft gain

Hike Pootatuck State Forest Loop

New Fairfield, Connecticut

1.8 mi / 259 ft gain

Hike Squantz Pond Trail

New Fairfield, Connecticut

2.2 mi / 321 ft gain

Corbin Hill and Pawling Nature Reserve via Appalachian Trail

Pawling, New York

12.11 mi / 1978 ft gain

Appalachian Trail: Metro North to Manitou

Pawling, New York

42.19 mi / 6348 ft gain

Places to stay

Holmestead Woods

Brewster, New York

Holmestead Woods

From $90 / night

Meadow Ridge Farm   Meadow

Litchfield, Connecticut

Meadow Ridge Farm Meadow

From $145 / night

Meadow Ridge Farm Woods

Litchfield, Connecticut

Meadow Ridge Farm Woods

From $135 / night

Creekside Solitude

Clinton Corners, New York

Creekside Solitude

From $75 / night

Northfield Brook Lake Group Shelters

Thomaston, Connecticut

Northfield Brook Lake Group Shelters

Hop Brook Lake Recreation Area

Naugatuck, Connecticut

Hop Brook Lake Recreation Area

Guides and stories

Earth Day 2020 Goes Online: How to Get Involved

Earth Day 2020 Goes Online: How to Get Involved

Jonathan Stull

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

Quick links