While it boasts architectural and historical marvels at virtually every corner, there’s a significant element of New York City where function trumps form. Subway cars, hot-dog carts, pizza joints, and Madison Square Garden — none of these iconic slices of the Apple are particularly pretty. Same with Belmont Park; you want bow ties and buskers, head to Saratoga Race Course.

Stonestreet Farm in central Kentucky has enjoyed a great deal of success at Thoroughbred racing’s highest level in a relatively short amount of time. Today, the farm founded by the late Jess Stonestreet Jackson is a full-service operation with breeding, training, and racing divisions. That growth was aided by two astute decisions Jackson made shortly after buying the former Buckram Oak estate in eastern Fayette County in 2005.