Appalachian Trail
(Easy, Moderate, or Strenuous)

Basset Loop
(Easy or Moderate)

Bennett's Pond
(Easy or Moderate)

Breadloaf Mountain
(Easy or Moderate)

Bull's Bridge
(Easy, Moderate, or Strenuous)

Caleb's Peak
(Easy or Moderate)

Cathedral Pines
(Easy)

Central Park (Manhattan)
New York City
(Easy, Moderate, or Strenuous)

Emily Griffith Beardsley
(Easy or Moderate)

Ersbacher Preserve
(Easy)

Flanders Nature Center
(Easy or Moderate)

Gerald Ivers
(Easy or Moderate)

Greenwich Audubon Center
(Easy or Moderate)

Hidden Valley
(Easy)

Huntington State Park
(Easy, Moderate, or Strenuous)

Housatonic Range Trail
(Easy, Moderate, or Strenuous)

Kent Falls
(Easy or Moderate)

Kettletown State Park
(Easy, Moderate, or Strenuous)

Lakeside Trail
(Easy)

Lilly Preserve
(Easy or Moderate)

Macedonia State Park
(Easy, Moderate, or Strenuous)

Mine Hill
(Easy or Moderate)

Milford Audubon
(Easy)

Mohawk State Forest
(Easy, Moderate, or Strenuous)

Mount Tom State Park
(Easy or Moderate)

New Caanan Nature Center
(Easy)

Orenaug Park
(Easy or Moderate)

Pine Knob Loop
(Easy, Moderate, or Strenuous)

Pond Mountain
(Easy or Moderate)

River Road Preserve
(Easy, Moderate, or Strenuous)

River Walk (Applachian Trail)
(Easy, Moderate, or Strenuous)

Saugatuck Valley Trails
(Easy, Moderate, or Strenuous)

Saugatuck Falls
(Easy or Moderate)

Schagticoke Mountain
(Easy, Moderate, or Strenuous)

Seth Low Peirrepont
(Easy or Moderate)

Sleeping Giant State Park
(Easy, Moderate, or Strenuous)

Southford Falls
(Easy or Moderate)

St. John's Cliffs
(Easy, Moderate, or Strenuous)

Steep Rock Association
(Easy, Moderate, or Strenuous)

Sunny Valley
(Easy)

Tarrywile Park
(Easy or Moderate)

Tory's Cave
(Easy)

Weir Farm
(Easy)

White Memorial
(Easy, Moderate, or Strenuous)

If you're also familiar with this region and want to suggest a hike or add some to the site please email  Berkshire Hiking.