Top Pick Your Own Farms & Fall Family Fun

Looking for a place in the Berkshires where you can pick your own apples and pumpkins? These small-family farms are ready to welcome you!

More than just places to pick some of the tastiest apples you’ve ever eaten or find the biggest pumpkin, Berkshire farms and orchards are destinations where you can ride a hay wagon, walk through a corn maze, eat cider donuts and ice cream, pet farm animals, taste artisanal ciders and wines, and shop for locally-produced foods. Add to that spectacular views and fresh mountain air and you’ve got the makings of a picture-perfect fall outing.

Ioka Valley Farm

In bucolic Richmond in the central Berkshires, Bartlett’s Orchard is open through Columbus Day or later, depending on weather and crop conditions. Early picking includes Macintosh and Paula Red. Don’t miss the cider donuts, apple cider, and delicious baked goods at the Farm Market Store. You can also pre-order available items online for curbside pickup or shipping.

As cooler weather settles into the Berkshires, there’s lots to enjoy at Hilltop Orchards & Furnace Brook Winery in Richmond. From apple picking to woodland trails to wine tasting and their own branded hard cider produced on-site, it’s a wonderful spot to spend an afternoon. The farm’s location is not only beautiful, it makes for ideal growing conditions for 27 apple varieties, including heritage and heirlooms from century-old trees. 

For pumpkins galore and farm-themed activities the whole family will enjoy, visit Ioka Valley Farm in Hancock. This 500-acre sustainable farm in the northern Berkshires is also home to a farm store, a mini corn maze, a giant pumpkin house, wagon rides, adult pedal carts, a pipeline slide, and fun games for all ages (you might even win a pumpkin).

High Lawn Farm

Historic High Lawn Farm in Lee is open daily to visitors and offers some of the most idyllic views in the Berkshires. Take a walk through the grounds and say hello to their Jersey herd before heading to the Farmstead Creamery Shop for an ice cream cone (voted Best in the Berkshires), farmstead cheeses, and ghee, all made with fresh milk from their cows. Be sure to take some time to go to the calf petting area.

There are so many delightful spots you can visit this fall for a taste of locally-grown and produced food. Ours is a partial list. For even more ideas, visit Berkshire Grown online for their guide to growers in the area, including pick-your-own favorites such as Whitney’s Farm Market in Cheshire, Jaeschke’s Orchard and Lakeview Orchard in Lanesborough, and Windy Hill Farm in Great Barrington. Wherever you go, be sure to let us know which one you ‘pick’!!

Know Before You Go: Picking conditions, hours, COVID protocols, and the need for advance reservations vary at each location. Check ahead.

Written by Nancy Macy

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