Hiking Trails in the Berkshires

BerkshireStyle sat down with Mike Dalton, Director of the Ritt Kellogg Mountain Program at Berkshire School and longtime resident of the Berkshires. He shared his most favorite trails and what makes the hiking experience in the Berkshires unique from anywhere else.

The Appalachian Trail - Throughout the Berkshires
Time and difficulty vary.
The AT is number one simply because it is one of the longest foot trails in the United States. Historically the region of the trail running through the Berkshires is unique for students of Berkshire School helped build it, blazing portions and constructing the Glen Brook Shelter lean-to. The AT extends over Mt. Greylock, the highest mountain in Massachusetts, as well as Mt. Everett, the second highest. Ultimately this trail stands at number one for its incredible scenic vistas.

The Ice Glen and Laura’s Tower - 1.5 mile round trip
A shorter hike in Stockbridge, the Ice Glen Trail is an interesting experience because, even if you walk it in June, it feels like February. It leads you through a gorge up to Laura’s Tower. From there you can enjoy glorious views of the Stockbridge Bowl and the rest of the Berkshires.

Alander Mountain - 8 mile round trip
In Mt. Washington State Forest, a longer, more difficult hike around the western extreme of the Taconics, with phenomenal views of the Catskill Mountains. .

Tyringham Cobble - 2 mile loop trail
In Tyringham, MA, on the Appalachian Trail and cared for by Trustees of the Reservation, Tyringham Cobble is a really neat, short hike. It’s a great day hike because it is a loop; you can park and then return right back to your car at the end of the day.

Monument Mountain - Several loop trails, 3 mile max
In Great Barrington, MA, another neat and extremely popular hike. From the summit enjoy great views of the Berkshires and the Housatonic River Valley.

Lime Kiln Farm - two loops, 0.75 or 1.8 miles
In Sheffield, MA and cared for by the Mass Audubon Society, this hike is absolutely beautiful. There, you find yourself in a field without a single house in sight. You truly feel as though you are in the middle of nowhere. In addition, Lime Kiln contains an historic component, an old limekiln on the premises.

What makes the hiking experience in the Berkshires unique from all other hiking experiences? According to Mike…

It’s the Berkshires’ incredible variety and diversity of plant life and vegetation. In a single hike, you can experience the beauty of mixed hardwood forest, coniferous forest and incredibly unique pitch pine forests with 50-75 year old trees resembling banzai.