 On 23 November 1897, he married Jane Marion Augusta Tracy.Wilmot's son, Reginald William Winchester "Chester" Wilmot (1911–1954), was a famed World War II correspondent and historian.His daughter, Jean Winchester Wilmot, married George Fisher Bemis, of Massachusetts, and emigrated to the USA, whence she sent back to the Australian Broadcasting Corporation, weekly "Letters from America", reporting on social, political and wartime life there.