Andy Shrake fixes windmills. Not the newfangled kilowatt-generating type, but the all-wood grain-grinding beauties built some 200 years ago. With 14 still standing on Nantucket, Cape Cod, and Rhode Island, repairing them is a full-time job. As Shrake’s name is passed along among preservation committees, he travels from mill to mill, fending off the ravages of weather and insects. “There’s no owner’s manual for these things,” he says. “You have to figure it out for yourself.” He gathers clues from old photos and other windmills in his care, and draws on a deep well of knowledge acquired over decades of conservation work.

The job shown here involved repairing the Jonathan Young Windmill in Orleans, Mass. Shrake used a chainsaw mill and a power planer to hew a new “dragger pole”; this 43-foot-long beam keeps the sails facing the wind while acting as a brace against its force. Inside the mill, the 6-foot-diameter brake wheel — named for the oak-drum brakes wrapping...

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