In 1828, through a chance introduction to the newly-formed Baltimore & Ohio Railroad, Winans became interested in this new style of transportation and developed railroad equipment whose basic design remained unchanged for well over a century. He is, for example, credited with placing wheel bearings on the outside of the truck, and with mounting a car on two four-wheeled trucks. He was, for a short time, an engineer with the B&O, and assisted Peter Cooper in constructing the Tom Thumb. A senior partner in a prestigious engineering firm until his retirement (1859), he spent most of his working life improving railroad machinery and developing new equipment such as the popular "camelback" locomotive. After his retirement, he became interested in marine transportation, and developed the "cigar steamer" whose legacy is the hull shape used in today's modern ocean liners.