Hiking near Pittsfield

These aren't in Pittsfield per se, but are just a drive away.

Every year, the Berkshires draw folks from all around the country to partake in its hiking. Even the Appalachian Trail comes through here.

    • Mount Greylock 🌟 (~15 min away)
      30 Rockwell Rd, Lanesborough, MA 01237 (directions)

      When the skies are clear, take a drive to the summit of Mount Greylock. You can do a little hike around there. The Appalachian Trail actually runs right through the summit.

      Lanesborough, MA
    • Monument Mountain (~20 min away)
      546 Stockbridge Rd, Great Barrington, MA 01230 (directions)

      A nice uphill and somewhat strenuous hike. Lots of parking, just north of Great Barrington. Pretty popular as well.

      Great Barrington, MA
    • Umpachene Falls (~37 min away)
      Umpachene Falls Rd, New Marlborough, MA 01259 (directions)

      A real local spot, the falls are wide and are just a few hundred feet from the parking area.

      New Marlborough, MA