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 August 23, 2023

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

Publisher's Note for 2023: Please be advised that recent and ongoing weather challenges in New England have significantly impacted local apple crops and, consequently, the ability of local businesses to offer apple picking opportunities. We kindly ask for your understanding and patience as these circumstances may lead to limited availability and changes in scheduling. The resilience of both the community and the orchards is greatly appreciated during these trying times.


Jaeschke’s Orchard, 23 Gould Road,  (413) 443-7180, (Will not be offering PYU this season, open 7 days a week)


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

Great Barrington

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


Bartlett’s Orchard, 575 Swamp Road, (413) 698-2559, (Will not be offering PYU this season. Farm store is open 7 days a week.)

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


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

Farther afield...

Apex Orchards, 225 Peckville Road, Shelburne, MA. (Open late-August through October from 10am-4pm, wagon runs on weekends only)

Clarkdale Fruit Farms, 30 Upper Road, Deerfield, MA. (Store open 9-5 daily)

Samascott Orchards5 Sunset Ave, Kinderhook, NY. (U-PICK HOURS: 8am-5pm* *last entry at 4pm CLOSED TUESDAYS)


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)