Outdoor Activities
Surrounded by the natural beauty of the Berkshires, The Red Lion Inn offers easy access to scenic hikes, waterfalls, gardens, and mountain views. Explore Monument Mountain, Mount Greylock, Bash Bish Falls, and more—perfect for fresh-air escapes in every season.
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Just minutes from The Red Lion Inn, Monument Mountain offers a rewarding hike with panoramic views of the Berkshires. This scenic trail is steeped in history and legend—it even inspired a hike by Herman Melville and Nathaniel Hawthorne. A must for nature lovers and literary buffs alike.
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As the highest peak in Massachusetts, Mount Greylock offers sweeping views across five states and miles of hiking trails, including a stretch of the Appalachian Trail. Just a short drive from The Red Lion Inn, it’s a favorite for outdoor enthusiasts, especially in the fall when the foliage is at its peak.
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The Ashuwillticook Rail Trail is a 12.7-mile paved path located on a former railway corridor. The trail traverses the towns of Cheshire, Lanesborough, and Adams, offering picturesque views of the Cheshire Reservoir and the Hoosic River. Public parking and restroom facilities are conveniently located at various access points along the route.
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Located just a short drive from The Red Lion Inn, Bash Bish Falls is Massachusetts' tallest waterfall, surrounded by lush forests and scenic trails. The easy hike to the falls rewards visitors with stunning views of cascading waters—a perfect spot for nature lovers and photographers alike.
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Stockbridge Bowl (Lake Mahkeenac) is a scenic 372-acre lake in Stockbridge, MA. It's a popular spot for boating, swimming, and enjoying the beautiful Berkshire views.
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Founded in 1895, this exclusive golf and tennis club is nestled in a tranquil mountain setting on the banks of the Housatonic River.
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This quiet, wooded 1.5-mile trail ascent winds through pines and hemlocks by Ice Glen (a glacial ravine) and ends at a summit tower with panoramic view of mountains in three surrounding states.
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A tree-to-tree adventure destination, eight aerial obstacle courses meander through the trees at various heights and include 15-17 elements including high wires, zip lines, and rope ladders.
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Enjoy scenic walking trails through woodlands and meadows, perfect for a relaxing stroll or a brisk walk. 2 With its peaceful atmosphere and beautiful surroundings, it's a great spot to unwind and connect with the outdoors.
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The area’s most popular ski resort also offers an off season aerial adventure park, mountain biking and an adventure park with mountain coaster, zip line, alpine slide and scenic chairlift rides.
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A leader in outdoor adventure offering white water rafting in Massachusetts and Vermont, zip line canopy tours in the Berkshires, plus kayaking and canoeing trips.
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During the winter months, experience excellent skiing and snowboarding across a variety of slopes catering to all skill levels. Night skiing under the lights adds an extra thrill to your evenings. As the seasons change, Bosquet transitions into an exciting adventure park. Soar through the trees on their zipline, challenge yourself on aerial obstacles, and enjoy other outdoor activities including concerts and food events.
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Ioka Valley Farm in Hancock is a family-owned destination offering fun for all ages! Enjoy seasonal activities, from picking your own strawberries and pumpkins to choosing the perfect Christmas tree. Visit the farm animals, explore the play area, and savor delicious maple syrup made right on site. With a rich history and beautiful setting, Ioka Valley Farm provides a memorable experience for the whole family.
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Step back in time at Hancock Shaker Village in Hancock, MA, a living history museum that brings to life the fascinating world of the Shakers. Explore beautifully preserved buildings, wander through the farm and gardens, and learn about the Shakers' unique way of life, craftsmanship, and spiritual devotion.
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Hilltop Orchards, a family-run orchard, offers a delightful escape with apple cider, wine tasting, and fresh cider donuts. Enjoy scenic hikes, explore the dog-friendly trails, and relax amidst the beautiful surroundings.
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Looking for high-flying thrills and family fun? Just over an hour from Stockbridge, Six Flags New England in Agawam lives up to its title as the Thrill Capital of New England. With roller coasters, water rides, and attractions for all ages, it’s the perfect day trip for adrenaline seekers and amusement park lovers alike.
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Ski Butternut in Great Barrington offers excellent skiing, snowboarding, and snow tubing for all levels. Enjoy well-groomed trails, beautiful Berkshire views, and a friendly atmosphere for a fantastic winter experience
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Berkshire East Mountain Resort in Charlemont offers year-round adventure in the Berkshires! In winter, enjoy skiing and snowboarding on well-groomed slopes, plus snow tubing for family fun. When the snow melts, the resort transforms into a hub for outdoor activities, including ziplining, mountain biking, and a thrilling mountain coaster. With scenic views and something for everyone, Berkshire East is a destination for all seasons.
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Otis Ridge is a beloved local ski area known for its welcoming, family-friendly atmosphere and vintage charm. Just about 35 minutes from the Red Lion Inn, it offers gentle slopes for beginners, affordable lift tickets, and a laid-back vibe that makes it perfect for a relaxed day on the mountain. Whether you're learning to ski or looking for a low-key adventure, Otis Ridge is a nostalgic winter escape.
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Catamount Mountain Resort is a year-round adventure destination just an hour from Stockbridge. In winter, enjoy skiing, snowboarding, and tubing across 44 trails. In summer, soar on the longest zipline in the U.S. or tackle the treetop Aerial Adventure Park. Perfect for family fun in every season!
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This stunning property in Windsor offers miles of trails perfect for hiking, cross-country skiing, and snowshoeing. Enjoy breathtaking views, diverse landscapes, and a peaceful escape into nature. A must-visit for outdoor enthusiasts in any season!