Woolford joined the Army at 19, and by 1800 he served under Ramsay when he commanded an expedition to Egypt.
He may have studied under Paul Sandby, professor of drawing at the Royal Military Academy.
Woolford left the Army in 1803, and worked for a decade as a landscape painter, in Edinburgh, until Ramsay hired him to be his draftsman, again, when he was appointed Lieutenant Governor of Nova Scotia.
[2][4] When Ramsay was appointed Governor General of British North America Woolford remained in Nova Scotia, where he worked to complete the buildings for Dalhousie College.
[1][3] In 1823 Ramsay arranged a sinecure for Woolford, when he was appointed assistant barrack-master in Saint John, New Brunswick.