Gainesway Neighborhood Association

The History of our Subdivision

History of the Gainesway Subdivision
by Scott Schultz (corner of Castleton Hill & Gainesway Dr )

John R. Gaines (1928 - 2005), a cornerstone figure in the Kentucky horse racing industry, was the owner of Overbrook Farm, formerly knows as Greentree farm, one of the largest horse farms in Lexington during its time. This 1500 acre property was home to many Thoroughbred horse racing champions, including the famous Aristides, the first horse to win the Kentucky Derby in 1875.

In 1982, John Gaines was instrumental in founding of the Breeder's Cup, an annual series of Thoroughbred horse races which has attracted race horses from around the world and helped to clean up the sport's image. Through 2006, the Breeder's Cup was a single-day horse-racing event and was later expanded to a two-day event in 2007. Although the Breeder's Cup venues change each year, all of its locations have been within the U.S., with the exception of one event in 1996 which took place at the Woodbine Racetrack in Canada. The Breeder's Cup was considered the richest single-day event in sports history, with race purses in excess of $20 million as of 2007. Currently the event is now referred to as the second richest day event in horse racing, following the inception of a new type of Thoroughbred racing in 2008 known as The Dubai World Cup Night, which features six races and a combined purse of $21 million.

When John Gaines sold the property to facilitate the development of what is now known as Gainesway Neighborhood, Overbrook Farm was then moved to its present location off Paris Pike in Lexington.

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