Jacob's Pillow began in 1790 as a hard-scrabble mountaintop farm at the top of a twisting, climbing stagecoach road between Boston and Albany. Local folk viewing the zig-zagging road from the bottom of the hill thought it resembled the rungs of a ladder, so these biblically minded New Englanders dubbed it "Jacob's Ladder".
Boulders dotted the farm pastures, among them a curiously-shaped one located behind the farmhouse. Given the rock "pillow" and the farm's proximity to "Jacob's Ladder", the Carter Family, who settled the property, furthered local allusions to the Book of Genesis (which tells of Jacob laying his head upon a rock and dreaming of a ladder to heaven) by giving their farm the name "Jacob's Pillow". The Pillow has long been a site of pioneering spirit, even before its establishment as a dance organization; in the mid-1800's the farm was known as a stop on the Underground Railroad for slaves escaping to Canada.