Your Guide to the Apple Picking in the Berkshires

A complete list of pick-your-own apple orchards in Berkshire County

By Berkshires Macaroni Kid September 20, 2022

Apple picking is a fall staple in the Berkshires, and we’ve compiled a list of some of our readers' favorite local orchards below. It is suggested that you call ahead just to make sure the orchards still have apples to pick, as apple season can be finicky around these parts.

Did I miss something? Please feel free to send me your favorite area orchard or patch via email at


Jaeschke’s Orchard, 23 Gould Road,  (413) 443-7180, (Picking begins Labor Day, open 7 days a week)


Bear Swamp Orchard & Distillery1209 B Hawley Road,, Check Facebook for PYO updates (Open Saturday & Sunday 1 p.m.-5 p.m. for curbside pickup at this time)


Jameson's High Meadow Farm, 410 Skyline Trail, (413) 354-9609, (Season begins mid-September, open 9 a.m. - 4 p.m. daily)


Lakeview Orchards, 94 Old Cheshire Road, (413) 448-6009,  (Open Wednesday-Monday, 9 a.m.-4 p.m. for picking)

Great Barrington

Windy Hill Farm, 686 Stockbridge Road, (413) 298-3217, (Season begins late August)


Bartlett’s Orchard, 575 Swamp Road, (413) 698-2559, (Opened for picking on Aug. 31 — Monday-Friday, 7 a.m.-5 p.m. and Saturday and Sunday, 8 a.m.-5:30 p.m.)

Hilltop Orchard, 500 Canaan Road, (800) 833-6274, (Open daily from 9 a.m.-5 p.m.). Hilltop is dog-friendly.


Riiska Brook Orchards, 101 New Hartford Road, (413) 258-4761, (Open Saturday and Sunday, 9 a.m.-5 p.m.)


Whitney's1775 S. State Road. - Route 8, (413) 442-4749,, (Open 7 days a week, 9 a.m.-6 p.m.)


Ioka Valley Farm3475 MA-Route 43, (413) 738-5915, (Open weekends from mid September - October)


Mountainview Farm, 45 Old Cheshire Road, (413) 770-6595,, Home of the $5 pumpkin! (Open Wednesday-Sunday 10 a.m.-5 p.m.)


Howden Farm303 Rannapo Road, (413) 229-8481, Home of the famous Howden pumpkins! (Call ahead for seasonal information)