Apples in the Berkshires
🍎 Fall in the Berkshires is unmatched! If you want to spend your autumn days apple picking, sipping fresh cider, and exploring the rolling hills, we've put together our favorite spots across the central and southern Berkshires. If you're looking for "pick-your-own" orchards, historic farm stores, or estate hard ciders paired with a great meal or local wine, here is our guide to experiencing the season.
1. Hilltop Orchards (Richmond) then... Balderdash Cellars
- The Experience: Sprawling across nearly 200 scenic acres, this historic farm offers miles of walking trails alongside its massive selection of pick-your-own apple trees. Come inside for some cider tasting where you are likely to be greeted by the fun David and Sara team!
- The Pairing: Just down the road, stop at Balderdash Cellars, where the team will welcome you to kick back on the lawn with bold wine, live music, and sweeping hillside views.
2. Bartlett's Orchard (Richmond) then... Proprietor's Lodge
- The Experience: Fill your baskets with crisp, locally grown apples and fresh-baked treats at Bartlett’s Orchard. Pick apples right in the trees, then head inside the country store for fresh-baked pies and local cider.
- The Pairing: Take a short, scenic drive over to Pontoosuc Lake to unwind with dinner and drinks right on the water at Proprietor's Lodge.
3. Windy Hill Farm (Between Stockbridge & Great Barrington) then... The Red Lion Inn
- The Experience: Set against the backdrop of the southern Berkshires, this diverse horticultural farm features a gorgeous 7-acre apple orchard ideal for a crisp autumn afternoon.
- The Pairing: Just minutes away in Stockbridge, cap off your day with a drink on the porch or a cozy meal at the historic The Red Lion Inn.
4. Sandisfield Orchard (Sandisfield) then... Sandisfield Arts Center
- The Experience: Fill your bags with fresh autumn apples right off the trees at this charming local orchard.
- The Pairing: Head over to the historic Sandisfield Arts Center to explore local culture, art exhibits, and community events inside a beautifully restored 19th-century building.
5. Little Apple Cidery (Hillsdale, NY) then... Hillsdale General Store
- The Experience: Tucked just over the border in nearby Hillsdale, this certified organic orchard specializes in crafting exceptional estate hard ciders under the trees.
- The Pairing: Head up the street a bit to the center of town to browse stylish homewares, local artisan goods, and lovely antiques at the Hillsdale General Store.
Final STOP: Berkshire House Stay
🏠 Your Home Base in the Berkshires: Why rush home
when you can make a full weekend out of it?
Located right in the center of Lee,
Berkshire House Stay is the ultimate cozy headquarters for your group getaway.
With plenty of space featuring 5 bedrooms and 5 baths, a fantastic private backyard, and a wonderful porch for morning coffee or evening unwinding, there is plenty of room for everyone to spread out and relax together.
✨ Ready to gather your crew? Share this page with your travel partners, plan your autumn escape, and come stay with us! Skip the platform fees and save 15% mid-week for Fall using code WEEKDAY15.