Outdoor Activities
The Berkshire Mountains are a haven for outdoor enthusiasts, offering a wide range of activities to enjoy the natural beauty of the region. Whether you're an adventurer, a nature lover, or someone seeking a leisurely outdoor experience, there's something for everyone.
Some of our Favorites
Hiking
Whether you're looking for a leisurely stroll or a challenging ascent, there's a hike for you in the Berkshires. When we feel like a hike but aren't sure where the closest one is, we use the All Trails app to find one. Here are a few of our favorites:
Mount Greylock
Standing as the highest peak in Massachusetts, Mount Greylock offers a network of hiking trails, including the Appalachian Trail, which passes through the summit. The views from the top are breathtaking, and the 92-foot War Memorial Tower is a prominent landmark.
Bash Bish Falls
This relatively short hike in Mount Washington State Forest leads to the stunning Bash Bish Falls, which is the highest single-drop waterfall in Massachusetts. The trail is well-maintained, and the payoff is the impressive cascading falls.
Tyringham Cobble
A moderately easy hike in Tyringham offers scenic views of the Housatonic River Valley. It's especially popular in the fall when the foliage is at its peak.
Benedict Pond Loop Trail
A serene hike around a peaceful pond. The forest is known for its diverse flora and fauna.
umpachene falls
If you're looking for a hike where you can get wet, this is for you. Walk alongside a river and find a pool to dip your toes in. Use caution as water levels can vary greatly.
Jiminy Peak Mountain Resort
With its variety of trails and terrain parks, Jiminy Peak is a favorite destination for skiers and snowboarders of all levels.
Bousquet Ski Area
This family-friendly ski area provides a welcoming environment for beginners and intermediate skiers, with both day and night skiing options.
Skiing
Skiing in the Berkshires transforms the region into a winter wonderland, offering thrilling downhill adventures and beautiful snowy landscapes. Whether you're a seasoned skier or a beginner, the Berkshires have slopes for everyone. Popular skiing spots include:
Ski Butternut
Known for its diverse terrain and snow tubing park, Ski Butternut offers winter fun for all ages.
Berkshire E Mountain Resort
In addition to its summer adventures, Berkshire East transforms into a winter wonderland with skiing and snowboarding, plus a thrilling mountain coaster.
Otis Ridge
Ideal for families and beginners, Otis Ridge provides a charming setting for a day on the slopes.
Biking
Biking in the Berkshires offers a fantastic way to explore the region's scenic beauty and charming landscapes. With a mix of trails, there's something for bikers of all skill levels to enjoy. Popular biking spots include:
Ashuwillticook Rail Trail
Enjoy a leisurely ride along this 11-mile paved trail that winds around the Cheshire Reservoir, providing beautiful lake views.
Berkshire Bike Path
This family-friendly trail meanders through picturesque surroundings, making it perfect for a relaxed ride.
Great Barrington River Walk
Lenox Bike Trail
Explore the charming town of Great Barrington while cycling along the Housatonic River on this scenic path.
Discover the town's beauty on this path that takes you through Lenox's scenic landscapes and historic areas.
Rock Climbing
Rock climbing in the Berkshires offers a thrilling adventure for outdoor enthusiasts and climbers of all levels. The region's unique geological features create exciting climbing opportunities. Popular rock climbing spots include:
Petticoat Lane
Farley Ledges
Climb in a beautiful forested setting with a mix of bouldering and top-rope climbing routes.
Known for its extensive rock climbing routes and variety of challenges, Farley Ledges is a popular destination for climbers.
Beartown State Forest
Combine hiking and rock climbing in this diverse forest with bouldering options suitable for various skill levels.
Ravine Ridge
Enjoy climbing challenges amid picturesque Berkshire scenery and a peaceful atmosphere.
Rattlesnake Mountain
This scenic area offers climbing opportunities with stunning views of the surrounding landscapes.
Rose Ledges
Climbing at Rose Ledges takes you through a narrow gorge with moss-covered rocks, providing a unique and shaded climbing experience.