Greenwood Raceway was a horse racing facility in Toronto.
Inaugurated in 1874 as Woodbine Race Course at the foot of Woodbine Avenue and Lake Ontario, it was owned and operated by two gentlemen named Pardee and Howell. Within a few years financial problems resulted in the property reverting to Joseph Duggan, the original land owner and retired innkeeper. In the early 1880s Duggan founded the Ontario Jockey Club (OJC). The facility hosted seasonal harness racing for Standardbred horses and flat racing events for Thoroughbreds.
Harness racing dates were transferred from Thorncliffe Park Raceway to Old Woodbine to fill the gap between the spring and fall thoroughbred meets, and the track was known as Greenwood Raceway during the harness meet. The track was at the junction of Kingston Road and Queen Street East, with only a narrow strip of land between it and Lake Ontario. Thoroughbred racing continued at Old Woodbine on a shortened six furlong (1,207 m) track. Harness races were at first conducted on the thoroughbred track, but serious problems with mud (including the starting gate being immobilized) led to the construction of a five-furlong (1006 m) stone dust harness track inside the thoroughbred track. This track was known for its tight turns and long back and homestretches.
In the early 1950s, the Ontario Jockey Club, led by directors E. P. Taylor, George C. Hendrie and J. E. Frowde Seagram, undertook an acquisition and consolidation program for southern Ontario racing. By 1956, the OJC operated just three facilities consisting of the Fort Erie Racetrack in Fort Erie, Ontario and two facilities in Toronto. A new facility for thoroughbred horse races was constructed in Toronto, and given the name Woodbine Racetrack. The Old Woodbine facility was completely renovated and renamed Greenwood Raceway in 1963. It held both harness racing and thoroughbred racing meets until its closure at the end of 1993.
Steeplechase races were held at Woodbine/Greenwood for a few years; There was a thoroughbred race announcer by the name of Foster "Buck" Dryden for several years.
A horse by the name of Last Mark, owned by James G. Fair of Cainsville, Ontario won the "Plate" in 1948, setting a new Plate record and only being equalled once, before the track was decommissioned. R.J. Speers' horse, Lord Fairmond came 2nd in that Plate race. Fair had 2 horses in that Plate which never ran in the Plate Trials but worked out between the 2 divisions of the "Trials". Their times were faster than the times of either of the trial divisions.
Greenwood Raceway was the site of the Canadian Pacing Derby, the North America Cup, the Fan Hanover Stakes, the Maple Leaf Trot, and the Canadian Trotting Classic.
In 1994, the thoroughbred and harness operations were moved to Woodbine. The stadium was demolished and replaced by residential and commercial development, including a betting parlour. Half of the property became Woodbine Park. To commemorate the history of the site, two of the new residential roadways were given names that reflected horse racing themes: Northern Dancer Blvd. (in honour of the famous thoroughbred Northern Dancer) and Winners Circle—a street which, paradoxically, runs in a straight line. Joseph Duggan Road was named after the historical landowner and Sarah Ashbridge Avenue commemorated another pioneer resident of the area.