Of his favorite places to paint in Maine, the artist writes, “One can’t help but wonder how many generations of pines and other trees have grown or perished here. And though those generations seem very long to us (they encompass many human generations), they are like a blink of an eye to those granite boulders, which were deposited about 15,000 years ago, during the last glacial period. Yet even the boulders have been gradually disintegrating from the slow, but relentless activities of solar radiation, acids secreted by lichens, and water that collects in the small cracks, freezing and expanding in winter, breaking the rock away in pieces. And as preamble to that, these boulders once traveled inside the glaciers, where they tumbled against other glacial debris, were smoothed and rounded, only to be rounded further now, by the elements.” It is these musings that keep Woolsey engaged in nature, and returning to it for his inspiration.
He received his BFA and MFA from the University of Pennsylvania, studying with Neil Welliver, Alex Katz, Elaine de Kooning, and Yvonne Jacquette. He has shown widely in Philadelphia, Boston, Chicago, and New York, and his work is in many private and corporate collections.