The first section, a 10-mile route between Pittsfield to Lenox (Massachusetts), opened in 2021. But there are plans to extend The High Road all the way across the ride of the Berkshire Mountains.
According to Lonely Planet, you can do this entire route in a day—without a car—and with stops at restaurants and a general store, just like one would do if hiking Europe’s pilgrim routes.
The concept of the walking holiday—a scenic foot journey on which you eat and rest in towns along the way, carrying little but a change of clothes, water and snacks—is integral to the High Road. The Berkshire Natural Resources Council, the land stewardship organization that created The High Road, found inspiration in Spain’s Camino de Santiago when fleshing out plans for their own town-to-town path.
The idea was to introduce Americans to this gentler, more accessible mode of traveling across the countryside by foot. While The High Road passes over bonafide mountains, the terrain never feels too rocky or steep. And the path’s immersive stretches through conservation woodlands are the perfect place to let your thoughts run wild and free.