👪 Family-Friendly in the Berkshires
- 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 - 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 - 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 - 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 - Hancock Shaker Village
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 - Berkshire Museum
39 South St, Pittsfield, MA 01201 (directions)A nice family-friendly museum in downtown Pittsfield. Great displays that highlight the local Berkshire flora and fauna.
Pittsfield, 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