Hiking Programs

mother and daughter hiking on mountain top with nice view

The Berkshires has some of the world's best hiking. Learn about the natural and cultural history of the Berkshires and local flora and fauna, all as you make your way to the areas best views.

Below, you will find some information about where we go, what to bring, and how to get there. Please visit our schedule and pricing page for information about the times and pricing of our programs.

What to bring

If you are joining us for a hiking program, it is important for you to be prepared. Please dress appropriately for the weather. On cold days, dress in layers so you will be warm enough. You will also need to be prepared for the sun. Bring a hat, sun glasses, and sun screen. It is also a good idea to bring a water bottle. Supportive footwear is recommended.

Locations and Directions

Our regularly scheduled trips are currently offered at three locations; Laura's Tower in Stockbridge, Monument Mountain in Great Barrington, and October Mountain State Forest in Lenox. Private bookings can be made for any of the trails in Berkshire County.

Laura's Tower, Stockbridge, MA

For GPS Directions, use Park Street, Stockbridge, MA and follow to end of street

From Downtown Stockbridge, take Route 7 South (South Street) 0.2 miles. Turn left onto Park Street at the Mobile Station. Follow Park Street to end. For driving directions from google, please enter your starting address below:

Monument Mountain, Great Barrington, MA

For GPS Directions, use 600 Stockbridge Rd. Great Barrington, MA which is the high school. The meeting point is just south of there on the West side of the street (Stockbridge Rd/Route 7)

From Downtown Stockbridge, take Route 7 South for three miles. Pass the high school on your left, going through both traffic lights. The meeting point is just a little farther on the right. For driving directions from google, please enter your starting address below:

October Mountain State Forest, Lenox, MA

For GPS Directions, use Roaring Brook Road Lenox, MA being sure that you are accessing it via New Lenox Road. Take Roaring Brook to the second Bridge which is the meeting point.

From Lee, MA at the I-90 Ramp, take Route 20 West being sure to follow the signs. After taking a right, continue up the hill passing through the downtown. Pass Laurel Lake on the left and Cranwell Resort on the Right. Merge onto Route 7 North/Route 20 West and proceed about 4 miles. Take a right onto New Lenox Road at a traffic light. There will be a store called "A Different Drummer's Kitchen" on the corner. At the stop sign, continue straight and cross the train tracks and the Housatonic River. Take your next right onto Roaring Brook Rd. The meeting point is at the second bridge. For driving directions from google, please enter your starting address below: