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Hiking in the Berkshires

Best Hiking Trails in the Berkshires

Looking for great year-round outdoor activities? Look no further than the hiking trails that wind their way through the beautiful Berkshires in western Massachusetts! The trails and woods are coming alive and there’s a whole world of outdoor exploration, discovery, and family adventures to be had this year.

Whether you’re after some entry level hiking, or a weekend family excursion, the following list offers a variety of local hiking opportunities, starting with one that’s right here in Bousquet’s own backyard.

Known for its fall foliage, there is still so much to enjoy in the spring and summer. Come to the mountain and hike the Mahanna Cobble trail, with its panoramic views of Pittsfield and the northern Berkshires, and then test your legs on one of these local hikes:

Spruce Hill, Savoy

With its woodland forests, an impressive cellar foundation, and expansive views in every direction, Spruce Hill is a hike that has it all! On 10,200 sprawling acres for year-round recreation.

Mount Greylock, North Adams, Lanesboro, Williamstown

There are too many great hikes here to choose just one, so the DCR has put out  this handy list of suggested excursions for all ages and abilities. Here you will find the highest point in Massachusetts, where you can see up to 90 miles away. 

Monument Mountain, Great Barrington

Rich in literary history, Monument Mountain is perfect for all ages. Walk in the footsteps of Hawthorne and Melville, and explore the boulders, cliffs and ledges at the summit. You may even see a bald eagle across the Housatonic River Valley from the 1,642-foot summit.

Olivia’s Overlook at Yokun Ridge South, Richmond

Olivia’s Overlook is at the center of the 734-acre Yokun Ridge reserve. This popular overlook is also the trailhead for 6 miles of trails. The BNRC has produced this helpful trail map to help guide your next adventure. These lands are of great significance to the Stockbridge-Munsee Mohican Nation today.

Shaker Mountain, Hancock

Transport yourself back to the 1800s on one of the hikes along the Shaker Trail, beginning at Hancock Shaker Village. Discover the remains of a former Shaker religious settlement and sacred site.  Enjoy a moderate-strenuous ability hike. 

Old Mill Trail, Dalton

This gentle 1.5 mile out and back trail follows the east branch of the Housatonic River, includes mill ruins, and offers .7 miles of accessible trail. This trail connects the communities of Dalton and Hinsdale and combines nature’s beauty with a rich local history.

If you’re still on the lookout for great outdoor experiences this spring, fall and summer, the Berkshires has so much more to offer, so be sure to explore these local Berkshire trails, or go big and check out the Appalachian Trail in Massachusetts.

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Head Snowmaker

jason phelps

Bio Coming Soon

head groomer

Nate Page

Bio Coming Soon

operations manager

jessica moulton

Jessica started at Bousquet in July 2021.

She grew up in North Adams and currently resides in Pittsfield with her partner and child. She has also lived in South Lake Tahoe, CA and Salt Lake City, UT while pursuing her dream of being a ski bum.

Jess has been skiing and snowboarding in the Berkshires since she was in middle school and also enjoys backpacking, paddle boarding, and biking while she’s not working.

She has a great passion for sharing outdoor recreation opportunities in Western Massachusetts with others.

Surface Manager

Josh Morse

Bio Coming Soon

on-hill programs manager

jeremy lawless

Jeremy started at Bousquet in September of 2021.

Ski & Ride School director

Cindy Bartlett

Cindy first started skiing at Bousquet when she was 7 years old and began teaching at the age of 14. She is a Level 2 certified PSIA instructor, and received her 40-year pin from PSIA-AASI two years ago. Cindy also met her husband at the mountain and has two kids who both learned to ski at Bousquet as well. 👨‍👩‍👧‍👦 Her passion is simply contagious as she continues to teach the next generation and share her love of skiing with all today.

Beyond Bousquet, Cindy is a volunteer and board member at Berkshire Humane Society 🐾 and rides horses. 🐴

🏔 Favorite trail: Roberto’s Chute
❤️ Favorite memory at Bousquet: a clinic with Court (a legendary Bousquet ski school instructor) when he told the boys, “Ski it like Cindy!”

mountain manager

nate bovard

Bio Coming Soon

Service & Rental Shop Manager

Jay Allen

Bio Coming Soon
general manager

kevin mcmillan

Kevin started at Bousquet in April of 2020. He brings 30 years of experience in the outdoor industry, along with a knack for creative problem solving and mad people skills.

He lives in Plainfield, and is an avid mountain biker and snowboarder.