AS THE LEAVES change their luster and let go , the hills of the Berkshires are flush with longstanding family farming and skiing traditions . From fresh apples plucked straight from the tree to snowy mountain adventures , local businesses are embracing innovation to continue providing memorable experiences for locals and visitors alike , with many evolving to meet the demands of an unpredictable climate . Here ’ s what a bushel of them are up to .
B y T a y l o r S t a u b a c h Orchards to Ski Slopes
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Courtesy of Hilltop Orchards
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FROM APPLE PICKING TO WHITE-MOUNTAIN ADVENTURES , THE BERKSHIRES HAS IT ALL
AS THE LEAVES change their luster and let go , the hills of the Berkshires are flush with longstanding family farming and skiing traditions . From fresh apples plucked straight from the tree to snowy mountain adventures , local businesses are embracing innovation to continue providing memorable experiences for locals and visitors alike , with many evolving to meet the demands of an unpredictable climate . Here ’ s what a bushel of them are up to .
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Jameson ’ s High Meadow Farm , a cherished local spot in Chester for over 60 years , embodies simplicity and tradition . Known for its sprawling blueberry fields and historic 75-year-old apple orchards , the farm welcomes families to pick their own fruit with 10 apple varieties , fostering cherished multi-generational memories . Visitors are greeted with farm-fresh eggs , cordwood , and maple syrup — available on the farm ’ s front porch all year round — while barnyard cows and errant tractors add to the authentic farm experience . Picking hours are daily from 9 a . m . to 4 p . m ., with payment accepted by cash or check only . On Facebook .
Windy Hill Farm , another local gem found in Great Barrington , offers pick-yourown apples and pears available until late October or early November . The farm ’ s scenic orchard provides stunning views of Monument Mountain and Beartown State Forest , complemented by a selection of fall flowers and festive items in their nursery and garden shop . The farm also hosts seasonal events , including fresh cider production starting around Labor Day . windyhillfarminc . com
Hilltop Orchards is three businesses rolled into 180 sprawling acres in
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