[4] The son of Arthur, former president of Stanley Woolen Mill, and Ann Kneass, Wheelock grew up in Uxbridge and graduated from Phillips Exeter Academy in 1961.

His father's side is descendant from Ralph Wheelock, attributed to be the forerunner of founding public education in the United States.

Wheelock's dissertation was titled "The Shifting Relationship of Perspective to Optics and its Manifestation in Paintings by Artists in Delft around 1650."

[5] Wheelock began his career in museums as a David E. Finley Fellow at the National Gallery of Art in 1973 and later was also named Research Curator, under director J. Carter Brown.

Wheelock married Susan Hoffman on June 13, 1964, with whom he had three children: Laura, Matthew, and Tobey.