
Where to Go Apple Picking This Fall: Your Guide to the Berkshires’ Best Orchards
As the crisp air of autumn sweeps through the Berkshires, there’s no better way to embrace the season than with a day spent apple picking. The rolling hills of Western Massachusetts are dotted with charming apple orchards, each offering its own unique experience. Whether you’re on the hunt for the perfect apple pie recipe or just looking to soak in the stunning fall foliage, here’s your guide to the best apple picking spots in the Berkshires this season.

Bartlett’s Apple Orchard: A Family Legacy in Every Bite
Tucked away in the quaint town of Richmond, Bartlett’s Apple Orchard has been a beloved destination for generations of apple enthusiasts. Though this season, due to an unexpected mid-May freeze, the orchard isn’t offering pick-your-own apples, it’s still a must-visit for anyone craving a true taste of fall. The farm store brims with freshly made cider donuts, cinnamon buns, and steaming hot cider, each bite a testament to the orchard’s four generations of farming excellence. Even if you can’t pick your own apples this year, the bounty of the orchard’s 13 apple varieties can still be enjoyed, making it a delightful stop on your autumn adventure.
Hilltop Orchards: Where Apples and Wine Make the Perfect Pair
Imagine picking apples with the breathtaking backdrop of the Berkshire Hills. That’s exactly what you’ll find at Hilltop Orchards, located on Route 295 in Richmond. This orchard is consistently voted one of the top five apple picking spots in Massachusetts, and it’s easy to see why. With 26 different apple varieties to choose from, your basket will overflow with the finest fruits of the season. And the experience doesn’t end there—Hilltop Orchards is home to Furnace Brook Winery, where you can indulge in a wine tasting, sip cider in a cozy Adirondack chair, and nibble on some of the best cider donuts around. It’s the perfect blend of rustic charm and gourmet indulgence, all while practicing eco-friendly farming methods that ensure the highest quality, residue-free apples.

Jaeschke’s Orchard: A Taste of History at the Foot of Mt. Greylock
Nestled in the shadow of Mt. Greylock, Jaeschke’s Orchard in Adams offers not just apples, but a slice of local history. This family-owned farm has been growing apples since 1881, and its prime location at the base of the mountain ensures that every apple is kissed by cool rainwater, resulting in an unbeatable flavor. As you wander through the orchard, it’s easy to imagine the generations that have tended these trees before you. After filling your basket, take a moment to relax with a picnic amidst the stunning natural beauty, or savor a glass of their sweet apple cider paired with a fresh cider donut from the farm store. Jaeschke’s Orchard is open from May to December, offering seasonal delights throughout the year, making it a place you’ll want to visit again and again.
Lakeview Orchard: Pick Your Own Apples with a View
For a day of apple picking with a side of spectacular views, head to Lakeview Orchard in Lanesborough. Perched above Hoosac Lake, the orchard offers sweeping vistas of the surrounding valley, making it a feast for the eyes as well as the taste buds. In addition to apple picking, Lakeview Orchard’s farm store is a treasure trove of homemade goods. From pierogi and golumpki to gnocchi and whoopie pies, there’s something to satisfy every craving. Their bakery is famous for treats like cider donuts and fruit scones, perfect for enjoying with a cup of hot cider. Beyond apples, the orchard also offers pick-your-own berries, tree fruits, and seasonal vegetables, making it a year-round destination for fresh, local produce.

Riiska Brook Orchard: A Hidden Gem in the Southern Berkshires
If you’re looking for a more secluded apple picking experience, Riiska Brook Orchard in Sandisfield is your perfect match. This hidden gem in the southern Berkshire Hills boasts over 2,700 semi-dwarf apple trees, offering ten different apple varieties for you to sample and select. The orchard’s family-friendly atmosphere is perfect for a relaxing day out, and you’re encouraged to taste the apples as you pick—an opportunity to discover new favorites. In addition to apples, Riiska Brook Orchard offers pumpkins, maple syrup, squash, and freshly squeezed cider, rounding out your visit with a full autumn harvest experience.

Frequently Asked Questions
What makes Bartlett’s Apple Orchard stand out?
Bartlett’s Apple Orchard, despite not offering pick-your-own apples this year, delights visitors with its freshly made cider donuts, cinnamon buns, and other farm-fresh treats, all crafted with the expertise of four generations of the Bartlett family.
Why is Hilltop Orchards a top choice for apple picking?
Hilltop Orchards offers more than just apple picking. It’s a destination where you can enjoy stunning Berkshire views, eco-friendly apple farming, wine tastings at Furnace Brook Winery, and delicious cider donuts, making it a complete fall experience.
What’s special about Lakeview Orchard?
Lakeview Orchard isn’t just about apples. With its panoramic views over Hoosac Lake and a farm store filled with homemade goods like pierogi, golumpki, and cider donuts, it’s a culinary and visual feast in the heart of the Berkshires.
Your Autumn Adventure Awaits
This fall, immerse yourself in the beauty and bounty of the Berkshires. Whether you’re a seasoned apple picker or new to the tradition, these orchards offer something for everyone. So grab your basket, pull on your coziest sweater, and head out to enjoy the apple picking season in Massachusetts—your perfect autumn day is just a short drive away.