The speakeasy became a favorite spot for influential writers, poets, playwrights, journalists, and activists, including members of the Lost Generation and the Beat Generation movements.
While attending Milford Mill Senior High school now Milford Mill Academy in Baltimore she played Mrs. Chumley in a production of Harvey, the wife to Dr. Chumley played by the now celebrity Ira Glass, of "This American Life".
Benson was born to Ralph Beaumont Benson (1862-1911), a member of the landed gentry, and Caroline Essex Cholmondeley (pronounced Chumley) at Lutwyche Hall in Shropshire in 1892.