Top Spots

Hike New Milford Reservoir Loop

New Milford, Connecticut

1.2 mi / 75 ft gain

Hike Waramaug Loop

New Milford, Connecticut

1.2 mi / 180 ft gain

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

Hike Roxbury Mines

Roxbury, Connecticut

3.6 mi / 511 ft gain

Hike Pinney Loop Trail

Washington, Connecticut

3.7 mi / 341 ft gain

Hike Green Circle Trail

Washington, Connecticut

4.2 mi / 521 ft gain

Hike Squantz Pond Trail

New Fairfield, Connecticut

2.2 mi / 321 ft gain

Hike Iron Ore Hill Red And Blue Loop

Bridgewater, Connecticut

2.5 mi / 459 ft gain

Places to stay

Brewster, New York

Holmestead Woods

From $90 / night

Litchfield, Connecticut

Meadow Ridge Farm Meadow

From $145 / night

Litchfield, Connecticut

Meadow Ridge Farm Woods

From $135 / night

Open Grange Coliving

Thomaston, Connecticut

Northfield Brook Lake Group Shelters

Naugatuck, Connecticut

Hop Brook Lake Recreation Area

Guides and stories

Earth Day 2020 Goes Online: How to Get Involved

Jonathan Stull

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

Quick links