The area east of The Maples Park was first known as Beard's Station, a stop on local stagecoach routes, before the coming of the railroad shortened the name to Beard and then to Crestwood in 1909 after locals grew tired of train engineers jokingly calling out “Whiskers.” The rolling countryside around Crestwood supported large-scale farming, and Oldham County farmers relied heavily on Louisville markets to sell their crops. Railroad tracks laid through town in 1869 let farmers ship local produce and goods from the depot. Wheat and corn were major crops, and threshing them required machinery that was scarce in the late 1800s, when only three steam-powered threshers were owned in all of Oldham County, so farmers often rented a neighbor's machine to separate the edible grain from the chaff or husk for bagging and sale. In 1901, the Interurban line linked Crestwood to Louisville and brought more business. In the 1950's, Crestwood became nationally known for producing orchard grass, and its importance led the South Oldham Lions Club to sponsor an annual Orchard Grass festival to promote the crop. Because The Maples had once been a small-scale farm, the park kept a farming theme, with many original structures remaining, including the Deibel Barn as a replica of the former Dairy Barn, farm-themed playground and sprayground features, and open rolling hills preserved like earlier pasture.