👪 Family-Friendly in Great Barrington

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
Butternut Ski Area
380 State Rd, Great Barrington, MA 01230 (directions)
Great skiing and snowboarding at Butternut. They have night snow tubing which is really excellent and family-friendly.
Great Barrington, MA

Family-Friendly nearby

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

Norman Rockwell Museum 🌟 (~12 min away)
9 Glendale Rd, Stockbridge, MA 01262 (directions)Stockbridge, MA
Hilltop Orchards (~20 min away)
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
Hancock Shaker Village (~25 min away)
1843 W Housatonic St, Pittsfield, MA 01201 (directions)
Lots of great history here and a small cafe/gift shop. In the winter, they set up an outdoor lights display that you can walk around in. It's really nice, and the old round stone barn is a must-see.
Pittsfield, MA