Serpentine Drive was an elaborately designed winding approach road to Earl W. Oglebay's estate, Waddington Farm, created in the grand manner of the great estates of industrialists and entrepreneurs such as Carnegie, Rockefeller, and Vanderbilt. Intended not for speed and convenience but for a pleasant, relaxing ride through a wooded landscape, it showcased the beauty of the property through glades, shrubbery, trees, horseshoe curves, stone walls, and a lookout. Although it appeared natural, every curve and planting was meticulously planned by landscape architects J. Wilkinson Elliott and Arthur Westcott Cowell of Pittsburgh, Pennsylvania, who visually closed in the drive so the estate would remain hidden until the top. Instead of ending with a dramatic view of the great house, the drive opened onto a view of the vegetable garden and the sweeping vista beyond, reflecting Earl Oglebay's passion for agriculture and presenting the estate as a working farm. Built and maintained as a private road for the Oglebay family and their guests, it contrasted with the more direct public approach of State Route 88, which was moved farther from the Mansion at Earl Oglebay's request after he purchased the property in 1900.