14 Must-Visit Best Hikes in the Berkshires You Will Love

The Berkshires of western Massachusetts are perfect for hiking. There are hundreds of miles of trails through beautiful scenery, making it a paradise for outdoor enthusiasts.

The area is known for its beautiful cities and vibrant culture, but it also offers amazing hiking trails of varying degrees of difficulty.

From strenuous hikes to laid-back walks in the woods, we are going to share the 14 best hikes in the Berkshires in this blog post. Keep reading!

Top 14 Best Hikes in the Berkshires

There are many great trails in the Berkshires. Each journey has its own unique charm. Mount Greylock, the highest mountain in Massachusetts, can be a tough climb.

Or, you can try the easy trails around Stockbridge which are great for families. There is a walk for everyone. Here are 14 of the best walks to enjoy in the Berkshires.

1. The Ledges Trail

Ledge Road in North Adams, Massachusetts. This is a great trip for those visiting the Berkshires. It is long and the Stony Ledge Trail is a short and steep hike that puts everything on a solid hiking check. As it has challenging terrain, quiet trails, remote camping and irresistible features.

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Miles

• 2.3-miles

Difficulty

• Hard

Nearby Attractions

• Brandywine Falls
• Boston Run Trail
• Haskell Run Trail

2. Saddle Ball Mountain Path

For those who want to take a strenuous hike with great views, the Saddle Ball Mountain Trail in Adams, Massachusetts is ideal. It is one of the best hikes in Massachusetts.

This loop trail takes you to the top of Saddle Ball Mountain. Here, you will enjoy breathtaking views of Mount Greylock and the beautiful Berkshire Mountains.

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Miles

• 7.6-mile loop trail

Difficulty

• Challenging

Nearby Attractions

• Camp 18 Logging Museum
• Seaside Aquarium
• Arcadia Beach State Recreation Area

3. Tyringham Cobble Loop

The Tyringham Cobble Loop is located in the heart of Berkshire County. This beautiful 2.1-mile trail showcases the area’s natural beauty without the rugged mountains.

The loop is flat and easy, making it great for families with young children or anyone who wants a leisurely walk in scenic surroundings.

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Miles

• 2.1-miles

Difficulty

• Moderate challenging

Nearby Attractions

• Bidwell House Museum
• Lee Premium Outlets
• McLennan Reservation

4. Pinnacle Trail to Laura’s Tower

The Pinnacle Trail to Laura Tower in Stockbridge, Massachusetts is a 1.8 mile commute. It takes you to one of the best locations in the Berkshires. The road is a bit challenging but there are breathtaking views from Laura Tower, the cliffs at the top of the Pinnacle in Stockbridge.

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Miles

• 1.8 miles

Difficulty

• Moderately challenging

Nearby Attractions

• Farmhouse Gallery & Gardens
• Rock Creek Park
• Buffalo Mountain Park

5. Monument Valley Loop

The Memorial Valley Loop is located in Great Barrington, Massachusetts. This trail is quite long and takes you through a variety of ecosystems.

You’ll love the beautiful nature of the Berkshires, with breathtaking views of forests, meadows, and rivers. Along the way, you can see clear mountains and valleys.

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Miles

• 3.2 miles

Difficulty

• Easy

Nearby Attractions

• Wildcat Trail
• John Ford’s Point
• Monument Valley Navajo Tribal Park

6. Savoy Mountain National Forest Road

Savoy Mountain State Forest has 4.5 miles of trails set up for you to explore. You will find peaceful forests, flowing rivers, and scenery.

Traveling is a beautiful way to enjoy nature. Whether you want an intense hike or an easy loop, Savoy Hill is considered the best hike in the Berkshires for beginners.

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Miles

• 4.5 miles

Difficulty

• Easy route

Nearby Attractions

• Art Museums
• Nature & Wildlife Tours
• River Rafting & Tubing

7.  Taconic Crest Trail to Berry Pond

It’s an challenging mile trail that goes there and back, through the beautiful Taconic Mountains offering breathtaking views of the surrounding valley and forest On a clear day, hikers can see the Adirondacks and Catskills from the summit of Berlin Mountain which is located in New York. It’s also one of the best hikes in the Berkshires for seniors.

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Miles

• 34.8 Miles

Difficulty

• Challenging

Nearby Attractions

• Hancock Shaker Village
• Barrington Stage Company
• Balderdash Cellars

8. The Glen Meadow Loop

It is located at the foot of the green mountain. There are a variety of landscapes along this route including forests, meadows, and rivers.

This is a relatively challenging route where you can enjoy beautiful scenery and relax in nature. The bulk of the Glen Meadow Loop is the Cataract. This waterfall is gorgeous, especially in the summer when the water is rising.

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Miles

• 1.7-mile

Difficulty

• Easy

Nearby Attractions

• Ashuwillticook Rail Trail
• MarketStreet Lynnfield
• Saugus Iron Works

9. The Hoosac Range Trail

The Hoosac Range Trail traverses the scenic Hoosac Range and offers spectacular views of the nearby mountains and is considered as the best hiking destination among hikers. The trail is a little steep, but the 6 mile round trip is a gradual climb with good views. There are steep spots and rocky areas, but the beautiful views from the gorge make it worth it.

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Miles

• 6 miles

Difficulty

• Moderately challenging

Nearby Attractions

• Bright Ideas Brewing
• Sanford Blackinton Mansion
• Clarksburg State Park

10. Ice Glen Trail

For a short & easy hike in the pleasant Berkshires, you should visit the Ice Glen Trail in Stockbridge, Massachusetts. The trail is 1.5 miles long and passes through a unique area called “Snow Glen.” Here, large boulders and dense vegetation keep it cool and shady even when it’s hot outside. The trail is also one of the best waterfall hikes in the Berkshires.

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Miles

• 1.5 miles

Difficulty

• Moderately challenging

11. Mount Everett Peak Trail

The trail is challenging, with some steep and rocky sections, but the spectacular view from the top makes it all worthwhile.

Mount Everett is the tallest mountain in southern Massachusetts. The views from the top are truly breathtaking. You can see 360 ​​degrees for miles. It has views of the Taconic Mountains, the Catskill Mountains, and even the Berkshires.

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Miles

• 17.5 miles

Difficulty

• Challenging

Nearby Attractions

• Night Shift Brewing
• Short Path Distillery
• Encore Boston Harbor Casino

12. Yokun Ridge South Loop

The Yokun Ridge South Loop is one of the best hikes near Lenox, MA. There is a mixture of different trails and scenery.

You will walk through beautiful forest, see great views, and follow a ridge line with beautiful views of the area. You can hike the Yokun Ridge South Loop at any time of the year. In spring, you can see wildflowers on the ground.

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Miles

• 1.6 miles

Difficulty

• Not too difficult

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. During this month, the leaves change color and are at their peak. You can get a wonderful view of the colorful foliage, making it a great choice for an autumn hike.

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Miles

• 6 miles

Difficulty

• Moderately challenging

Nearby Attractions

• Rocky Mountain National Park
• Wildlife Tour
• Grand Lake

14. Windsor Jambs Trail

Windsor Jambs Road in Windsor exudes peace and vitality. One of the best parts of the Windsor Jambs trail is the picturesque waterfall after which the trail is named.

The path descends into a ravine. From there you can enjoy a breathtaking view of water flowing over mud-covered rocks.

See Map: Get Directions

Miles

• 2.1 miles

Difficulty

• Easy

Nearby Attractions

• Wahconah Falls
• Mahican-Mohawk
• Appalachian Trail

Final Thoughts!

If you want to get into the beautiful Berkshires with some great adventures, these top 14 best hikes in the Berkshires will offer breathtaking views and exciting experiences. You can choose from the tranquil Ledges Trail to the more challenging Taconic Crest Trail. Each trip offers a special nature adventure.

Whether you prefer an easy hike or a challenging climb, the Berkshires have something for every adventure enthusiast. Put on your boots, pack what you need, and get ready for a great adventure through these diverse landscapes that showcase the area’s natural beauty.

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