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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 topographic trail print
Taconic Skyline Trail
The Berkshires
Holy Mount Trail topographic trail print
Holy Mount Trail
The Berkshires
Shaker Mountain Loop Trail topographic trail print
Shaker Mountain Loop Trail
The Berkshires
Pine Mountain Loop Trail topographic trail print
Pine Mountain Loop Trail
The Berkshires
Potter Mountain Trail topographic trail print
Potter Mountain Trail
The Berkshires
Doll Mountain Trail topographic trail print
Doll Mountain Trail
The Berkshires
Smith Mountain Trail topographic trail print
Smith Mountain Trail
The Berkshires

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