Top Spots

Hike Pomperaug Trail

Oxford, Connecticut

3.7 mi / 856 ft gain

Hike Zoar Trail

Newtown, Connecticut

6.1 mi / 1 ft gain

Hike Webb Mountain Yellow/Orange/Red Loop

Monroe, Connecticut

1 mi / 157 ft gain

Hike Webb Mountain Trail

Monroe, Connecticut

1.6 mi / 118 ft gain

Hike Jackson Cove

Oxford, Connecticut

1.1 mi / 167 ft gain

Hike Rockhouse Hill Sanctuary Loop

Oxford, Connecticut

4.6 mi / 643 ft gain

Hike Pomperaug And Crest Trail Loop

Southbury, Connecticut

3.4 mi / 606 ft gain

Hike Miller Trail

Southbury, Connecticut

2.5 mi / 393 ft gain

Hike Pomperau Trail Loop

Southbury, Connecticut

1.6 mi / 285 ft gain

Places to stay

Naugatuck, Connecticut

Hop Brook Lake Recreation Area

Open Grange Coliving

Thomaston, Connecticut

Northfield Brook Lake Group Shelters

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

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