Top Spots

Hike Stratton Brook Old Railroad Pathway

Simsbury, Connecticut

2.5 mi / 42 ft gain

Hike Orange Blazes, Blue Blazes, Yellow Blazes, White Blazes

Simsbury, Connecticut

2.7 mi / 265 ft gain

Hike Orange Blazes

Simsbury, Connecticut

1.2 mi / 98 ft gain

Hike Yellows Blazes To Blue And Yellow Blazes

Simsbury, Connecticut

2 mi / 114 ft gain

Hike Massacoe Hike

Simsbury, Connecticut

1.4 mi / 52 ft gain

Hike Beldon Forest

Simsbury, Connecticut

1.5 mi / 127 ft gain

Hike Farmington Canal Heritage Trail: Simsbury To Floydville Road

Simsbury, Connecticut

5.1 mi / 131 ft gain

Hike to the Heublein Tower on Talcott Mountain

Simsbury, Connecticut

2.5 mi / 500 ft gain

Hike Penwood State Park Trail

Simsbury, Connecticut

10.3 mi / 1 ft gain

Places to stay

Thomaston, Connecticut

Northfield Brook Lake Group Shelters

Maple Corner Farm's Meadow Site

From $120 / night

Litchfield, Connecticut

Meadow Ridge Farm Woods

From $135 / night

Litchfield, Connecticut

Meadow Ridge Farm Meadow

From $145 / night

Naugatuck, Connecticut

Hop Brook Lake Recreation Area

New Marlborough, Massachusetts

Echo Hill

From $150 / night

Guides and stories

Escape to These 8 Private Campsites in Massachusetts’ Berkshire Mountains

The Outbound Collective

Quick links