On a crisp autumn morning not too long ago, I walked out the front door of my room at the Red Lion Inn just off Main Street and headed in the direction of a forest, where in 10 minutes I’d be hiking along the Housatonic River.

It seemed like a wild idea, exploring the area so freely without four wheels. I was in a small town called Stockbridge in the middle of the Berkshires, a place that had long epitomized car-dependency. My parents had raised me on stories of adventure, including those 1970s Charlemont road trips to a perfect cabin in the woods. I had envisioned their car (I think it was a Volvo station wagon), regularly stocked with wine, beef, and friends, as the way to escape city life. Taking a car never seemed like anything but the only option to get to the Berkshires

 

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