He studied at the University of Chicago,[3] where he was a member of a literary circle including Elizabeth Madox Roberts, Yvor Winters, and Janet Lewis, but left after contracting Spanish flu.

Wescott and Wheeler returned to the United States and maintained an apartment in Manhattan with photographer George Platt Lynes, whom they had met in France in 1926.

When his brother Lloyd moved to a dairy farm in Union Township, near Clinton in Hunterdon County, New Jersey, in 1936, Wescott along with Wheeler and Lynes took over one of the farmhand houses and named it Stone-Blossom.

The Midwest-born author seems to slide into the golden handcuffs of expatriate decadence: supported by the heiress his brother married Barbara Harrison Wescott,surrounded by literate friends, given to social drinking and letter-writing.

[6] In 1959, when his brother Lloyd acquired a farm near the village of Rosemont in Delaware Township, Hunterdon County, New Jersey, Wescott moved into a two-story stone house on the property, dubbed Haymeadows.