The Berkshires is a veritable playground, with hilly terrain for hiking and taking in panoramic views, meandering trails and wildlife preserves for communing with nature, rivers and lakes for paddling and fishing and swimming, and ski resorts and cross-country trails for winter activities.
Hiking/Biking
Appalachian Mountain Club (Berkshires Chapter)
Appalachian Trail Conservancy (the AT runs through CT, MA, and VT)
Ashuwillticook Rail Trail
Berkshire Bike and Board (bike rentals and routes)
Berkshire Cycling Association (suggested routes)
Berkshire Hiking.com
Berkshires Natural Resources Council (for top hikes along with maps and trails)
Harlem Valley Rail Trail
Housatonic Heritage Bike Routes
Mass Audubon (Pleasant Valley Wildlife Sanctuary)
Skiing
Bousquet Mountain
Bromley
Butternut
Catamount
Jiminy Peak
Magic Mountain
Mount Snow
Notchview
Okemo
Smuggler’s Notch