The Berkshires region of Western Massachusetts is perfect for hiking, with hundreds of miles of trails through beautiful scenery making it a paradise for outdoor enthusiasts.
The region is known for its beautiful cities and vibrant culture, but it also offers fantastic hiking trails of varying difficulty levels.
From strenuous hikes to leisurely strolls through the woods, this blog post will introduce you to 14 of the best hiking trails in the Berkshires. Read on!
Top 14 Hiking Trails in the Berkshires
The Berkshires are home to many amazing trails, each with its own charm. Climbing Mount Greylock, the highest mountain in Massachusetts, can be tough.
Or you could try one of the easy family-friendly trails around Stockbridge. There’s a walk for everyone. Here are 14 of the best walks in the Berkshires.
1. Ledge Trail
Ledge Road, North Adams, Massachusetts. Visit the BerkshiresStony Ledge Trail features long, short and steep hikes, all of which qualify for a solid hiking check. It offers challenging terrain, quiet trails, secluded campsites and charming features.
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Nearby attractions
- Brandywine Falls
- Boston Run Trail
- Haskell Run Trail
2. Saddleball Mountain Pass
If you’re looking for a strenuous hike with great views, Saddle Bowl Mountain Trail in Adams, Massachusetts is ideal. It’s one of the best hiking trails in Massachusetts.
This loop trail leads to the summit of Saddle Bowl Mountain, where you’ll enjoy breathtaking views of Mount Greylock and the beautiful Berkshire Mountains.
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Nearby attractions
- Camp 18 Logging Museum
- Seaside Aquarium
- Arcadia Beach State Recreation Area
3. Tillingham Cobble Loop
Tillingham Cobble Loop is located in the heart of Berkshire County. This beautiful 2.1 mile trail allows you to see the natural beauty of the area, minus the rugged mountains.
The loop is flat and easy, making it perfect for families with young children or anyone wanting a leisurely stroll amid beautiful scenery.
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Nearby attractions
- Bidwell House Museum
- Lee Premium Outlets
- McLennan Conservation Area
4. Pinnacle Trail to Laura’s Tower
The Pinnacle Trail to Laura Tower in Stockbridge, Massachusetts is a 1.1 mile commute that takes you to one of the best parts of the Berkshire region. Although the trail is a little challenging, you’ll enjoy breathtaking views from Laura Tower, the cliff at the top of Stockbridge’s Pinnacle.
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Nearby attractions
- Farmhouse Gallery and Gardens
- Rock Creek Park
- Buffalo Mountain Park
5. Monument Valley Loop
Memorial Valley Loop is located in Great Barrington, Massachusetts. This trail is fairly long and takes you through a variety of ecosystems.
You’ll love the natural beauty of the Berkshires, with breathtaking views of forests, meadows and rivers, and crystal clear mountain and valley views along the way.
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Nearby attractions
- Wildcat Trail
- John Ford’s take
- Monument Valley Navajo Tribal Park
6. Savoy Mountain National Forest Road
Savoy Mountain State Forest has 4.5 miles of trails to explore. Enjoy tranquil forests, flowing rivers, and views.
Traveling is a great way to enjoy nature, and whether you’re looking for a strenuous hike or an easy loop, Savoy Hill is considered the best hike in the Berkshires for beginners.
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Nearby attractions
- Museum
- Nature and Wildlife Tours
- River Rafting & Tubing
7. Taconic Crest Trail to Berry Pond
beautiful Taconic Mountains There are breathtaking views of the surrounding valley and forests, and on a clear day you can see the Adirondack and Catskill Mountains from the top of Berlin Mountain in New York, as well as some great hiking trails for seniors in the Berkshires.
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Nearby attractions
- Hancock Shaker Village
- Barrington Stage Company
- Balderdash Cellars
8. Glen Meadow Loop
Located at the foot of lush mountains, it offers a variety of landscapes including forests, grasslands and rivers.
This is a fairly challenging route, but it offers beautiful views and a relaxing nature experience. A large part of the Glen Meadow Loop is the Cataract, a waterfall that is spectacular, especially in summer when the water level is high.
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Nearby attractions
- Ashwilticook Rail Trail
- Market Street Lynnfield
- Saugus Iron Works
9. Hoosac Mountain Trail
The Hoosac Mountain Trail is considered a top hiking destination among hikers because it traverses the scenic Hoosac Mountains and offers spectacular views of the nearby mountains. The trail is a little steep, but the 6-mile round trip is a gradual climb with great views. It can be steep and rocky in places, but the beautiful views from the valley make it worth it.
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Nearby attractions
- Cultivating bright ideas
- Sanford-Blackington Mansion
- Clarksburg State Park
10. Ice Glen Trail
If you’re looking for a short, easy hike in the pleasant Berkshires, try the Ice Glen Trail in Stockbridge, Massachusetts. The trail is 1.5 miles long and passes through a unique area called “Snow Glen,” where large rocks and dense vegetation keep you cool and shaded even when it’s hot outside. This trail is also one of the best waterfall hikes in the Berkshires.
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11. Mount Everett Peak Trail
The trail is steep and has some rocky sections, making it challenging, but the amazing views from the top make it worth it.
Mount Everett is the highest mountain in Southern Massachusetts. The views from the top are truly breathtaking, with 360 degree views for miles around. You can see the Taconic Mountains, the Catskill Mountains, and even the Berkshire Mountains.
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Nearby attractions
- Night Shift Brewing
- Short Path Distillery
- Encore Boston Harbor Casino
12. Yokun Ridge South Loop
Yokun Ridge South Loop is one of the best hikes near Lenox, Massachusetts, offering a diverse mix of trails and scenery.
You’ll walk through beautiful forests, take in amazing views, and follow the ridgeline for beautiful views of the area. You can hike the Yokun Ridge South Loop any time of the year. In the spring, you’ll see wildflowers blooming on the ground.
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Nearby attractions
- Tanglewood
- Norman Rockwell Museum
- The Mount, Edith Wharton’s Home
13. Deer Mountain Road
Deer Mountain Trail offers beautiful views of the Berkshires. October is one of the best times to hike this trail. This is the month when the leaves begin to change color and reach their peak. You can enjoy the amazing views of the colorful leaves, making this a great fall hike.
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Nearby attractions
- Rocky Mountain National Park
- Wildlife Tours
- Grand Lake
14. Windsor Jams Trail
The Windsor Jambus Road in Windsor is full of peace and vibrancy. One of the best things about the Windsor Jambus Trail is the beautiful waterfall that the trail is named after.
The path descends into a valley where you can enjoy breathtaking views of water cascading over muddy rocks.
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Nearby attractions
- Wahcona Falls
- Mahican Mohawk
- Appalachian Trail
lastly!
If you’re looking for a great adventure in the beautiful Berkshires, these 14 best hiking trails in the Berkshires will give you breathtaking views and exciting experiences. Choose from trails ranging from the tranquil Ledge Trail to the more challenging Taconic Crest Trail, each offering a special kind of natural adventure.
Whether you prefer easy hikes or challenging climbs, the Berkshires have something for every adventurer, so lace up your boots, pack your essentials and get ready to venture into diverse landscapes that showcase the region’s natural beauty.
FAQ
What is the highest peak in the Berkshire region?
Mount Greylock is the highest peak in the Berkshires.
What are the most popular mountains to hike in New Hampshire?
Mount Monadnock is often cited as the busiest peak due to its central location and spectacular views, but experts flock to Mount Washington, which stands 6,288 feet tall and is more challenging.
What are the best trails in Black River State Forest?
One of several marked trails within Black River State Forest, Castle Mound Nature Trail is one of the most popular and highly regarded by all who walk it. For more moderate hikes, there are the Norwalk, Wild Cat, Red Oak Loop and Black River State Forest Loop Trails.
Are there any waterfalls at Ricketts Glen?
Of course, you know Ricketts Glen has some big waterfalls: With over 20 named falls, it’s a hiker’s dream.
Are there any waterfalls on Grandfather Mountain?
Grandfather Mountain is home to a number of incredibly beautiful waterfalls – Linville Falls is probably one of the most popular, even though it’s technically just outside the park boundaries – and there are also smaller, hidden waterfalls around the mountain that can be accessed by a number of hiking trails.
