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Hiking in the Berkshires: Optimal’s Favorites!

Optimal's Favorite Hiking Spots - Summer in the Berkshires

Summertime in the Berkshire’s: Our Favorite Hiking Spots

Summer bursts into vibrant life in the Berkshires, and what better way to celebrate than by exploring its scenic trails? Here’s our list of fantastic hikes, ranging from family-friendly adventures to challenging treks with breathtaking views:

1. Steven’s Glen (West Stockbridge)

• Location: Just outside West Stockbridge village center.

• Description: A moderate 1.2-mile loop trail through a hemlock forest with a cascading waterfall – Lenox Mountain Brook – as the highlight. Perfect for a refreshing summer hike with a touch of scenic wonder.

• Length: 1.2 miles (loop)

• Difficulty: Moderate

2. Clam River Reserve (Sandisfield)

• Location: Sandisfield, about a 20-minute drive from Great Barrington.

• Description: The Trustees of Reservations manage this sprawling preserve with over 8 miles of hiking trails. Choose from various options, like riverside strolls, or moderate climbs, with views of the surrounding valley.

• Length: Trails range from 1 to 4 miles (various loops and out-and-back options)

• Difficulty: Easy to Moderate

3. Thomas Palmer Brook (Great Barrington)

• Location: Great Barrington, with access points on both Monument Valley Road and Alford Road.

• Description: This Trustees of Reservations property offers a moderate 2.5-mile loop trail along a scenic brook. Lush forests and cascading waterfalls create a peaceful ambiance, perfect for nature enthusiasts.

• Length: 2.5 miles (loop)

• Difficulty: Moderate

4. Ice Glen Trail (Stockbridge)

• Location: Stockbridge, with the trailhead located at The Trustees of Reservations property – The Field.

• Description: A short but captivating 0.6-mile round-trip walk through a cool ravine with waterfalls and unique rock formations carved by glaciers. A refreshing escape on a hot summer day, that also isn’t too long.

• Length: 0.6 miles (round-trip)

• Difficulty: Easy

5. The Cobbles (Cheshire)

• Location: Cheshire, with access via the Appalachian Trail.

• Description: This moderate 3.4-mile loop trail on the Appalachian Trail offers scenic overlooks. In addition, rock scrambles are available for the adventurous people seeking a little challenge. Enjoy stunning views of the surrounding mountains and valleys when you reach the summit.

• Length: 3.4 miles (loop)

• Difficulty: Moderate (with some challenging sections)

6. Mount Greylock State Reservation (Lanesboro)

• Location: Lanesboro, the highest peak in Massachusetts.

• Description: Finally, the crown jewel of the Berkshires, Mount Greylock offers multiple trails for all skill levels. Hike to the summit (via Bellows Pipe Trail for a challenging but rewarding experience) for panoramic views, or choose a shorter scenic trail for a more leisurely outing.

• Length: Trails range from 3 to 8 miles (various options)

• Difficulty: Easy to Difficult (depending on the chosen trail)

Click on each title to be redirected to their google maps location. If you find yourself needing a tune up before or after your hike, then click here to schedule a relaxing optimal recovery massage or relieving pain management massage.

Remember: Before you hit the trails, make sure to check the weather conditions, wear proper footwear and clothing, and pack plenty of water and snacks. Happy hiking!

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