The Berkshires of western Massachusetts are a truly magical place that both locals and visitors enjoy.

Tucked in the far west corner of Massachusetts, Berkshire County spans the length of the state, bordering Vermont, New York, and Connecticut. The mountains offer stunning views throughout the year, cultural hubs and historic landmarks provide an abundance of shows, exhibitions, and activities, and the culinary landscape is spectacular. It's no surprise that close to three million people visit on an annual basis.

While tourism in The Berkshires really peaks in the summer, Fall is the most stunning time of year. The fall foliage is like none other. Numerous prestigious travel magazines have named it the most beautiful in the world. That natural beauty, combined with perfect autumn weather and plenty of options for our favorite fall activities, it's no surprise that folks from all over the world flock to the Berkshires, Massachusetts in October.

One A-list celebrity who is no stranger to the Berkshires took time over the past holiday weekend to partake in one of our favorite fall activities, apple picking!

Today Show Host Al Roker Spend Holiday Weekend Apple Picking in The Berkshires, Massachusetts

Beloved Today Show host Al Roker, who spends much of his time in the Berkshires was apple-picking at popular Hilltop Orchards and Furnace Brook Winery in Richmond, Massachusetts.

The Roker family owns a home just outside the Berkshires over the state line in New York and, as shared on his personal Instagram account, he spent Indigenous Peoples Day weekend with his children and new grandchild.



Nestled at the foothills of the Berkshires and on the border of upstate New York, Hilltop Orchards is a 187-acre working farm with an orchard-to-can cidery, winery, and tasting room. They're proud to sustainably grow our many apple varieties and other fruits at the orchard. This time of year the orchard is open daily for apple picking and wine and cider tastings.

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Gallery Credit: Laura Ratliff


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