September 26th, 2023

Berkshires Apple Orchards Perfect for Apple Picking

Whoever said “An apple a day keeps the doctor away” must have been from the Berkshires. In the fall, the trees transform into a tapestry of oranges, yellows, reds, and browns creating a picturesque show of fall foliage that can only be seen in New England. Local Berkshire farms and orchards coat the landscape, making for multiple perfect afternoons without having to visit one twice. Here are our top few you won’t want to miss!

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Hilltop Orchards

When researching where to go this fall for pick-you-own, you may find that May 2023 was an unfortunate month for apple orchards in the Berkshires because of a frost mid-month, but many orchards made it and have flourishing PYO crops, not to mention an abundance of other fun activities—one of which is Hilltop Orchards

This PYO hotspot is well-known for its age-old history, breathtaking views, and the seemingly never-ending supply of apples. They also offer artisanal ciders and award-winning wines made from their on-site fruits. Come for the apple picking, stay for the cider tastings. Be sure to grab your picking tickets in advance through their website

Windy Hill Farm

This picturesque apple-picking orchard in Great Barrington has a limited supply this year due to the harsh early spring frost but is planning to have a PYO season nonetheless. Wander through their orchard and you’ll see why it’s so beloved by locals and visitors alike. They also offer homemade pressed cider, stunning views of fall foliage, a seasonal garden center and shop, and more. If you’re a nature lover in search of a way to celebrate the changing of the seasons, this apple orchard in MA is for you.

Jaeschke’s Orchard

If you couldn’t tell by now, apple picking in the Berkshires is one of our favorite fall activities. This is why we pay a visit to Jaeschke’s Orchard, year after year. Offering 33 varieties of hybrid, standard, and heirloom apples on their 55-acre orchard, this third-generation family-owned farm has perfected the art of apple picking and growing in its 130 years in the business. Whether you’re looking to pick Honeycrisp, Northern Spy, Macoun, or Winter Banana, or you’ve never even heard of any of those varieties, you’re in the right place. 

Stay at the Briarcliff Motel

After you’ve carefully selected your fruits, gotten your fill of warm apple cider, and savored as many cinnamon sugar-covered cider donuts as you can get your hands on, return to a place that feels just as warm and cozy as your own home. The Briarcliff Motel is the perfect place to gather around the fire pit in your favorite sweater or sip warm tea before slipping into a restful sleep after a long day of apple picking in the Berkshires. Book your stay with us this autumn.