 He owned the Dufferin Park Racetrack, Hillcrest Racetrack and Long Branch Racetrack, and was a partner in the Kenilworth Park Racetrack at Windsor, Ontario, and the Thorncliffe Park Raceway in Leaside, Ontario.Orpen was well known as a facilitator of gambling, first at his hotel, and eventually at a casino in Mimico, Ontario.After his death, his family continued the horse-racing businesses until the 1950s, when they sold their tracks during a time of consolidation of racetracks in Ontario.