Custom Hikes

I will design a Berkshire hiking experience for your abilities, your interests and your time schedule.


Many options are available:

Beginner--Learn to Hike
An easy and fun morning or afternoon walk for beginner hikers than includes learning about walking on the trail, how not to get lost, how to pee in the woods and not get your feet wet (that's for us ladies), and how to avoid ticks, bears and other forest critters. Get all your questions about hiking answered!
Time: 1.5 to 2 hours. Charge: $75 for up to 4 participants.
Contact Berkshire Hiker

Advanced Beginner Hike
A morning or afternoon walk on the trail with moderate climbing to a destination of your choice such as a mountain top, wilderness lake, etc. Get a review of hiking skills including "leave-no-trace" ethics.
Time: 2 to 3 hours. Charge: $100 for up to 4 participants.
Contact Berkshire Hiker

Intermediate Hike
Approximately 5 miles on wonderful trails with views or waterfalls or special places. Get a review of hiking skills including "leave-no-trace" ethics. The trail will have moderately strenuous sections. May be on the world-famous Appalachian Trail.
Time: 3 to 4 hours. Charge: $125 for up to 4 participants.
Contact Berkshire Hiker

Advanced Hike
A day-long hike on the Appalachian Trail which has 90 miles in the Berkshires, or on the Taconic Trail which traverses the Taconic Mountains on the border of New York State.
Time: To be agreed upon. Charge: To be agreed upon.
Contact Berkshire Hiker

Weekly Hike
We set up a day and time to meet for a weekly hike. It's an outdoor alternative to training in the gym. You learn about hiking, enjoy the benefits of being on the trail and take care of your body, all at the same time!
Time: To be agreed upon. Charge: $40/hr.
Contact Berkshire Hiker


Bess Dillman
413-528-4130


One of many Berkshire "micro-views," a beautiful garden unaided by human hand!
View northward from the Appalachian Trail; a wide expanse of trees, hills, mountains and lots of sky.

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