A Perfect Fall Escape in the Berkshires: Top Autumn Activities for Guests at the Red Lion Inn 

As the vibrant colors of fall sweep across the Berkshires, guests at the historic Red Lion Inn in Stockbridge are treated to more than just the changing leaves, with activities ranging from the active—like apple picking and visiting a huge regional festival—to more relaxed (think: warm cider doughnuts and farms stands). Whether you're staying in a cozy room, suite, or one of the Village Houses at Red Lion Inn, here’s a guide to the best autumn activities that will elevate your fall getaway in Stockbridge.

Start your adventure at Hilltop Orchards in Richmond, nestled in the Berkshire hills, where guests can go apple picking and munch on freshly made cider doughnuts. The blissful crisp air and scenic views make it easy to see why this is a favorite for Red Lion Inn guests in the autumn. Don’t forget to pick up some of Hilltop’s famed hard cider before you leave! Another local gem for apple picking and produce, Windy Hill Farm in Great Barrington, is a family-run farm home to picturesque orchards with a wide variety of apple trees. Windy Hill also offers pumpkins, gourds, and other seasonal decor to help you get your home in the harvest season spirit. And no fall stay at the Red Lion Inn would be complete without a visit to Bartlett’s Orchard in Richmond. Famed for its cider doughnuts, homemade pies, cider, and vast selection of apples, Bartlett’s is a local institution. For the best in seasonal produce, including apples, squash, and pumpkins, Taft Farms in Great Barrington is a standout. This family-run farm is also home to a bakery renowned for its delicious pies and cookies. Their corn maze is a hit with families.

The Big E festival, which runs from mid-September to early October in Springfield is the largest fair in New England, celebrating the culture, food, and agriculture of the region. From massive cream puffs to thrilling rides, livestock shows, and craft exhibits, The Big E has something for everyone. Returning to your quiet, beautifully appointed room or suite at the Red Lion Inn is the perfect ending to time at the lively fair, and makes for a beautiful representation of time in the Berkshires—melding excitement with tranquility.

Autumn is a beautiful time to be outdoors in the Berkshires and the Berkshire Botanical Garden in Stockbridge offers a serene escape to take in stunning fall foliage and learn more about the region’s trees, plants and flowers. The garden's annual Harvest Festival features local artisans, food vendors, and children’s activities.

Whether you’re apple picking, indulging in freshly baked cider doughnuts, or taking in the rich tapestry of fall colors, your stay at the Red Lion Inn offers unparalleled access to the best of Berkshires in autumn. With every apple picked, doughnut savored, or festival attended, you’ll create lasting memories that tie together the beauty and flavors of the season with the comfort and elegance of your stay at the Red Lion Inn. Book Your Stay and experience fall magic!

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The Best of Berkshires Autumn Traditions at The Red Lion Inn

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Shopping in the Berkshires: A Guide to the Best Stores, Boutiques and Shops—With The Red Lion Inn as Your Hub