Top Spots

Hike Squantz Pond Trail

New Fairfield, Connecticut

2.2 mi / 321 ft gain

Hike Great Hollow And Lower Overlook Loop

New Fairfield, Connecticut

4 mi / 800 ft gain

Hike Pootatuck State Forest Loop

New Fairfield, Connecticut

1.8 mi / 259 ft gain

Hike Pine Hill Road Loop

New Fairfield, Connecticut

1.9 mi / 291 ft gain

Hike Great Hollow Main Loop

New Fairfield, Connecticut

2.4 mi / 288 ft gain

Hike Boggs Pond Red Trail Loop

Danbury, Connecticut

3.4 mi / 600 ft gain

Hike Still River Greenway: Arthur Harris Linear Park

Brookfield, Connecticut

3.3 mi / 131 ft gain

Hike Williams Gurski Open Space Trails Via Williams Park

Brookfield, Connecticut

3 mi / 462 ft gain

Hike Parks Pond Loop

Danbury, Connecticut

1.3 mi / 137 ft gain

Places to stay

Brewster, New York

Holmestead Woods

From $90 / night

Open Grange Coliving

Naugatuck, Connecticut

Hop Brook Lake Recreation Area

Downing Wood

From $165 / 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

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