Writer and environmentalist Lauren R. Stevens is a regular Eagle contributor.

The problem: How to get across the Taconic Range between what was to become New York State and a nascent Massachusetts. You could go north, following a water level route on the Hoosic River through Pownal, Vt. South of that, your best choice was to look for low points, passes, saddles.

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Lauren R. Stevens is author of “50 Hikes in the Berkshires,” Countryman Press/W.W. Norton, 2016.