Within 37 mi of Pittsfield, Massachusetts · 7 trails
Trails near Pittsfield, as prints.
The country around Pittsfield has 7 trails with full pages in our collection, 21 miles of trail in all, Taconic Skyline Trail and Holy Mount Trail among them. The longest is Taconic Skyline Trail at 13.3 miles, also the biggest climb at 1,503 ft of gain. 6 are under 5 miles, so there is a short day here too. Each one is a custom topographic print drawn from the route's real elevation data, every switchback and every foot of climb, made to order. Every print from $39, free US shipping.

Taconic Skyline Trail
The Berkshires

Holy Mount Trail
The Berkshires

Shaker Mountain Loop Trail
The Berkshires

Pine Mountain Loop Trail
The Berkshires

Potter Mountain Trail
The Berkshires

Doll Mountain Trail
The Berkshires

Smith Mountain Trail
The Berkshires