Fall in the Berkshires

Fall foliage season is in full effect this time of year. Leaf peepers from all around come to the Berkshires to hike, pick apples and find the best, hottest, freshest apple cider donuts around.


  • 🍩 Apple Cider Donuts

    Apple cider donuts are a Berkshires speciality that you see only during Fall Foliage season. There are about a dozen farms/stores in the county that make them fresh on the weekends mostly. Always best when hot.

    • Taft Farms 🌟
      119 Park St, Great Barrington, MA 01230 (directions)

      Really the absolute best, freshest apple cider donuts in the Berkshires. Also a really nice little farm store.

      Great Barrington, MA
    • Riiska Brook Orchard
      101 New Hartford Road, Sandisfield, MA 01255 (directions)

      Local, family-owned farm with apple-picking.

      Sandisfield, MA
    • Ioka Valley Family Farm
      3475 Hancock Rd, Hancock, MA 01237 (directions)

      In the spring, they make maple syrup at the farm. You can get pancakes here as well. In the winter, it becomes a Christmas tree farm.

      Hancock, MA
    • Hilltop Orchards
      508 Canaan Rd Richmond, Richmond, MA 01254 (directions)

      Fresh apple cider donuts in the fall, with a nice view of the moutains. They also do ciders and wines.

      Richmond, MA
    • Bartlett's Orchard
      575 Swamp Rd, Richmond, MA 01245 (directions)

      Big orchard in the hills between Great Barrington and Pittsfield. Great if you are on your way north to Greylock. Really serene, so quiet. Big market inside. They were making the apple cider donuts fresh while we were there.

      Richmond, MA
    • Jaeschke Orchards
      23 Gould Rd, Adams, MA 01220 (directions)

      Right at the base of Mt. Greylock (with an incredible view of the peak) the orchard has apple picking and cider donuts on the weekends.

      Adams, MA
    • Whitney's Farm Market
      1775 S State Rd, Cheshire, MA 01225 (directions)

      Great farm store with a ton of pumpkins in the fall and activities for the kids to do, like goats and a playground. Great apple cider donuts as well.

      Cheshire, MA
  • 🍎 Apple Picking

    Plenty of farms let you come and pick your own apples, which can be a lot of fun for the whole-family.

    • Riiska Brook Orchard
      101 New Hartford Road, Sandisfield, MA 01255 (directions)

      Local, family-owned farm with apple-picking.

      Sandisfield, MA
    • Windy Hill Farm
      686 Stockbridge Rd, Great Barrington, MA 01230 (directions)

      Great little spot just north of town. Has apple picking and pumpkins during the fall.

      Great Barrington, MA
    • Hilltop Orchards
      508 Canaan Rd Richmond, Richmond, MA 01254 (directions)

      Fresh apple cider donuts in the fall, with a nice view of the moutains. They also do ciders and wines.

      Richmond, MA
    • Bartlett's Orchard
      575 Swamp Rd, Richmond, MA 01245 (directions)

      Big orchard in the hills between Great Barrington and Pittsfield. Great if you are on your way north to Greylock. Really serene, so quiet. Big market inside. They were making the apple cider donuts fresh while we were there.

      Richmond, MA
    • Jaeschke Orchards
      23 Gould Rd, Adams, MA 01220 (directions)

      Right at the base of Mt. Greylock (with an incredible view of the peak) the orchard has apple picking and cider donuts on the weekends.

      Adams, MA
  • 🍁 Fall Foliage

    The Berkshires are known for their bright colors during autumn, drawing "leaf peepers" from the cities of New York and Boston each year.

    • Mount Greylock 🌟
      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
    • Hairpin Turn
      1935 Mohawk Trail, Clarksburg, MA 01247 (directions)

      The historic Hairpin Turn is at the end of the Mohawk Trail and has a little restaurant at a pull out with a great view of the mountains.

      Clarksburg, MA