Thousands of years ago, Indigenous peoples lived and travelled along the Don River. The river’s fertile valleys and abundant wildlife made it an ideal location for fishing, hunting, and gathering. Archaeological evidence shows that the Don River valley was part of a vast network of Indigenous trade and travel routes that connected Lake Ontario to the northern territories. These communities built seasonal camps and villages near the riverbanks, relying on its waters not only for sustenance but also as a means of transportation and cultural connection long before European settlement in the Toronto area.
In 1831, British settler John Taylor and his family established their home in what is now known as the Thorncliffe Park area of Toronto. The community takes its name from Thorn Cliff House, the family’s first residence in the region and a symbol of their growing influence in 19th-century Toronto. Built on a sprawling 82-acre property situated at the Forks of the Don Valley, the estate reflected both the industrious spirit and the ambitions of the Taylor family. Over time, the Taylors became prominent figures in Toronto’s development, particularly through their contributions to the city’s milling and paper industries. The landscape of Thorncliffe Park, with its elevated views and proximity to the Don River, offered both strategic and aesthetic advantages making it an ideal location for the Taylor family to begin their legacy.
The Taylor family became one of the most influential industrial families in the Don Valley area. Over time, they acquired control of several mills, including sawmills, paper mills, and gristmills, which played a major role in Toronto’s early economic growth. They also established and operated the well-known Don Valley Brick Works, which produced millions of bricks used in constructing many of Toronto’s landmark buildings. In addition to their industrial ventures, the Taylors owned and managed thousands of acres of land across the Don Valley, transforming it into a hub of manufacturing and agriculture.
In the early 1870s, Robert T Davies married Margaret Matilda Taylor, the daughter of John Taylor. In 1901, after his wife’s family encountered financial difficulties, Davies acquired most of the Taylor family’s holdings in the Don Valley, including two paper mills and the Don Valley Brick Works. By the time of his death in 1916, Davies was one of the wealthiest people in Toronto.
As a boy, Davies developed a love for horse racing and for a while was a jockey in Thoroughbred flat racing. He established a horse breeding farm where Thorncliffe Park is now.
In 1917, the Thorncliffe Park Raceway was constructed on the plateau overlooking the Don River Valley. It quickly became one of Toronto’s premier horse racing venues, featuring a grand oval track, modern stables, and grandstands that attracted large crowds from across the city. The raceway hosted numerous prestigious events and served as a social and entertainment hub during the early 20th century. Its establishment marked the beginning of Thorncliffe Park’s transformation from farmland owned by the Taylor family into a vibrant recreational and community space.
Under the banner of Thorncliffe Stable, owner and racing enthusiast Robert Davies managed and raced both thoroughbred and standardbred horses, contributing significantly to Toronto’s early horse racing scene. Thorncliffe Park Raceway became known for its lively competitions and high standards of racing excellence. Among the notable thoroughbred events held at the track were the Prince of Wales Stakes, one of Canada’s most prestigious races, the My Dear Stakes, which showcased promising young horses, and the Clarendon Cup, a long-standing favourite among local racing fans. These events helped establish Thorncliffe Park as an important centre for Canadian horse racing during the early 20th century, attracting breeders, jockeys, and spectators from across the country.
The Thorncliffe Park Raceway tickets were often printed on sturdy cardstock and featured distinctive designs, including the name of the raceway, the date, and sometimes illustrations of horses or jockeys in action. Collecting these tickets became a popular pastime for racing enthusiasts, as they not only granted access to the races but also acted as keepsakes reflecting the excitement and social importance of horse racing in early 20th-century Toronto.
Spectators at Thorncliffe Park Raceway came from all walks of life, gathering to experience the thrill of horse racing in the early 20th century. The grandstands were often filled with families, socialites, and devoted racing fans who cheered for their favourite horses and jockeys. Many visitors dressed in their finest attire, reflecting the raceway’s reputation as both a sporting venue and a social event. Spectators not only watched the races but also participated in the excitement of betting, discussed the latest racing news, and enjoyed refreshments and entertainment offered on site. The lively crowds contributed to the track’s vibrant atmosphere, making Thorncliffe Park Raceway a central hub of recreation, social interaction, and community engagement.
The Raceway continued to operate as a hub for horse racing and social gatherings until 1952, when the property was sold to the Ontario Jockey Club, marking the end of an era for the historic track. On June 23, 1952, the final thoroughbred race was held, bringing to a close decades of competition, excitement, and community life centered around the track.
Harness racing at Thorncliffe Park Raceway remained active for several months after thoroughbred racing had ended, continuing to draw drivers, horses, and enthusiastic spectators until August 12, 1953. On that day, the final harness race was held, closing the chapter on the track’s long-standing contribution to Toronto’s horse racing scene. The end of harness racing marked the complete cessation of sporting events at Thorncliffe Park Raceway, paving the way for the track’s sale and eventual transformation, while leaving behind memories of a vibrant era in the city’s recreational and sporting history.
During 1930s, ski jumping gained high popularity in southern Ontario and a lot of new ski jumps were built. In 1933, Toronto Ski Club didn’t want to lag behind other clubs and thus also built their own ski jump at Don Valley in Thorncliffe in January 1934.
It hosted the Ontario Champion Ski Jump competition, drawing about 10,000 spectators. However, by February 1941 the last event was held, and subsequently the jump was dismantled.
After the closure of Raceway and the end of its recreational use, the property underwent a major transition in ownership. It was eventually transferred to a land development company called Thorncliffe Park Limited, which marked the beginning of a new chapter in the site’s history. The company’s acquisition signaled a shift from entertainment and sporting purposes to residential and urban development, laying the groundwork for the transformation of the former raceway and surrounding lands into what would eventually become the modern Thorncliffe Park community. This transfer reflected broader trends in mid-20th-century Toronto, where expanding urban populations and industrial growth prompted the redevelopment of former recreational and agricultural lands.
The Jockey Club Condominiums, a 21-storey residential building was completed in 1991 by Overon Investments Limited. The area around Overlea Boulevard underwent significant changes in the latter half of the 20th century.
The development of the Jockey Club was part of a broader trend in Toronto during the late 1980s and early 1990s, where former industrial lands were repurposed for residential use. This transformation was influenced by factors such as urbanization, population growth, and changing land-use policies that encouraged higher-density development near transit corridors.
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