There are several ski resorts, numerous lakes, ponds and rivers, museums, pick-your-own orchards, music festivals, arts, and cultural program.

Running past the Berkshire Hills School is the Ashuwillticook Rail Trail. This former railroad route was converted into a 10-foot wide paved bike, walking and roller blading path. The Rail Trail runs parallel to Route 8 by Cheshire Lake, through wooded areas, and along streams from Lanesboro to Adams, Massachusetts. For more information about the trail, click here.