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Best Hiking Trails in the Berkshires

Best Hiking Trails 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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Guest Service Manager

Amanda Cozzaglio

Amanda started at Bousquet in September, 2022.

She was born and raised in the Berkshires and currently resides in Pittsfield. She loves to be outside in the summer months hiking the various trails we have to enjoy, biking on the Rail Trail or kayaking anywhere there is water. Although she enjoys the warm weather over the cold, she is excited to appreciate the winter beauty on a whole other level and brush up on her skiing skills!

When Amanda is not working, she thoroughly enjoys spending time with her family (mainly her 5 nephews and 1 sweet little niece 😊)

Yaron Steinhauer enjoying activities at Bousquet Mountain
operations manager

Yaron Steinhauer

Yaron’s been in the Snowsports industry for 20 years, starting out as an instructor at Hunter Mountain. He leveled up with his Level 3 PSIA certification, then headed out west for a bit. Now he’s back east and has been our Operations Manager since the summer of 2023! He’s all about sharing his passion for the sport and making sure everyone enjoys their time on the snow.

Originally from Westchester County, NY, he’s now hanging out in the Berkshires, and if he’s not on the slopes, he’s probably biking around the hills (especially in the summer).

Smiling woman leaning against a textured tree trunk outdoors on a sunny day, partial face visible.
marketing + Sales Manager

Coby Porter

Coby, a native of Lanesborough, MA, learned how to ski at Bousquet and has a deep love for the outdoors. She earned her Bachelor’s Degree in Communications with a focus in New Media and is currently pursuing her MBA.

For Coby, Bousquet is more than just a job. It is a way to combine two passions: the outdoors and advertising. Having grown up at Bousquet, she knows firsthand the impact the mountain can have on the community. Being part of Bousquet is a full-circle moment, giving her the opportunity to help create the same magic of learning, growing, and falling in love with the mountain for the next generation.

Smiling man in a gray hoodie outdoors, with a blurred green background; hoodie shows 'BOUSQUET' text.
Office Manager

Zack Senecal

Zachary, a native of Lenox, MA, brings a strong background in hospitality and customer service, with a passion for creating welcoming and memorable experiences. He holds an Associate Degree in Hospitality Management from Berkshire Community College and was drawn to Bousquet because of the mountain’s unique sense of community and its ability to bring people together.

He is excited to bring his hospitality experience, positive attitude, and people-first approach to the Bousquet team. Zachary hopes to help make every visit to the mountain feel special while contributing to the welcoming atmosphere that makes Bousquet such a special part of the Berkshires.

Ski & Ride School director

Michael Sheinkman

Michael joined the Bousquet Snowsports team following retirement from a 30 year career responding to disasters and humanitarian crises around the world with the United Nations and the US government. He first started skiing at 5 years old, improving his skills during family trips to Vermont. Michael currently holds PSIA certifications as a Level 1 Ski Instructor and Children’s Specialist and has instructed professionally at Bousquet, Catamount, and Killington.
 
Beyond Bousquet, Michael enjoys cross-country skiing, hiking. bicycling, swimming, and SCUBA diving.
 
Favorite trail: Grand
 
Favorite memory at Bousquet: Telemark skiing down Grand through untracked snow.
Autumn landscape at Bousquet Mountain with colorful foliage
mountain manager

nate bovard

Nate Bovard has served as Mountain Manager at Bousquet Mountain since 2020.

Prior to joining Bousquet, he worked in mountain operations at both Sugarbush Resort and Berkshire East Mountain Resort, bringing experience from two well-established New England ski areas.

He is responsible for all on-mountain operations, including lift operations, snowmaking, grooming, trail maintenance, and outside facilities.

Nate oversees seasonal mountain operations staff and plays a key role in ensuring the mountain operates safely and efficiently while supporting capital improvement projects and long-term operational planning

Scenic view of hiking trail at Bousquet Mountain
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.