The Berkshires - Guided Adventures
Guided Hikes, Biking & Boating
Don’t want to worry about trail navigation, logistics, or packing heavy gear? These local experts take all the stress out of the planning and lead the way so you can just focus on the experience.
Berkshire Adventure Tours
Berkshire Adventure Tours offers guests small-group excursions that showcase our stunning region from a totally unique perspective.
- Scenic E-Bike Picnics: The two hour, beginner-friendly guided rides wind through the scenic backroads of the Richmond countryside or along a completely paved rail trail with zero car traffic.
- Private Captain-Led Lake Escapes: A private two-hour floating lounge experience out on the pristine local waters. A professional captain handles all the navigation so you can anchor and enjoy a peaceful, calm spot for an afternoon of swimming and lakeside relaxation.
How to book:
- Call: 413-281-9602
- Book Online: Berkshire Adventure Tours
🌲 Professional Hiking Guide
Jeff, "The Tie-Dyed Guide": For those who want a truly tailored trek, we highly recommend working with our trusted local partner for private excursions. Based in North Adams, Jeff is a dedicated Berkshire mountain trail guide with nearly a decade of hiking experience and six years as a professional guide. He is fully safety-certified with Wilderness First Aid and CPR/First Aid training. Whether you want to climb a peak or wander through the fragrant forest canopy, Jeff excels at creating an accessible, enjoyable adventure for all ages and abilities. He loves sharing the simple pleasure of nature and helping guests achieve their own personal summit.
- How to book:
- Book Online: Tie-Dyed Guide
Signature Treks in the Berkshires
I’m Olivia! I spend my weekdays teaching middle schoolers and weekends exploring the mountains.
I love all things outdoors, from hiking to long drives. I grew up in the suburbs of Dallas with parents who left Europe with their own sense of adventure and their sights set on America. I’ve embraced their spirit and taken my travels all over. I traveled to Peru alone and hiked to Machu Picchu along the Inca trail.
With every new year comes an updated list of places to visit, words to learn, and experiences to have. I can customize a local Berkshires hike for you. Do you want to enjoy the Appalachian Trail without doing 2190 miles of it? Do you want to enjoy some ponds and lakes in the area? Reach out, let me know. Lets go on a day adventure. Send a note: [email protected]
Host Tip: These activities, especially the guided trips, can fill up quickly during peak summer weekends. We highly recommend booking your mountain adventure passes and guided sessions at least a week before your arrival to ensure availability.
Planning your visit? Berkshire House Stay is located close to it all. Staying with us means most everything is within 15 minutes, making your trip even more seamless. Click here to check availability: BHS Availability