👪 Family-Friendly in Cheshire

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

Family-Friendly nearby

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

Mount Greylock 🌟 (~5 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
Jaeschke Orchards (~12 min away)
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
Berkshire Museum (~15 min away)
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