Haapy Trails Guiding

The Berkshires premier
guiding service

Leading outdoor adventures since 2000

  • Odin and NIkki

    Having lived in far off places like Nairobi, Singapore and Chennai, Odin is now happy to call the Berkshires home. An avid mountain biker, telemark skier and trail builder he brings 12 years of guiding experience and enthusiasm on every outing.

  • Simon rocking the single speed

    Simon's interest in the natural world and sharing that enthusiasm has kept him guiding for the past 16 years. As a cycling enthusiast, there is not a road in Berkshire county he has not peddled, winter or summer! Simon is our most requested guide.

  • Nikki showing her tele skills

    In addition to being an outdoor enthusiast, Nikki has been a massage therapist since 1999 as well as an Ayurvedic Educator and Consultant. She believes that spending time in nature is a very important component to one's health. There is nothing she loves more than spending a summer day on the water and dropping a knee in the winter.

  • Sonja and friend

    An avid hiker with many, many miles on the AT. High energy and a smile for every mile, Sonja will keep you entertained and educated on all things outdoors.

  • John enjoying a break

    Originally from Minnesota, John has called the Berkshires home for 10 years. Mountain biking and XC skiing he cannot get enough of and yes, John is another dog lover so Sal may be along for the next trip as a trail-side companion.

  • Abby and a sunset

    As a native of the Berkshires, Abby has had the opportunity to explore multiple mediums of recreation throughout her life. With over ten years of guiding experience at Canyon Ranch facilitating hiking, kayaking, canoeing, skiing (nordic and alpine) and biking (road and mountain), Abby has the local knowledge that you are looking for. Her appreciation of the Berkshires is reaffirmed each and every time she is able to take advantage of this landscape set apart.