For many years the town was known for its Riverside Race Track. The Riverside Park Jockey Club operated from 1928 to 1937 and was popularly called “Pendergast Track” after its patron Big City Boss Tom Pendergast (although Pendergast was not officially on its organization papers). The horse racing track was on the site of a former dog racing track. The track operated under a questionable legal basis. The site was supplanted by an automobile race track which closed in the 1990s.
A legal gambling establishment on the river now is the $106 million casino run by Argosy Gaming Company.
One of the landmarks in Riverside is the Riverside Red X store. It was founded as a gas station in 1948 by Edward Young. Over time, Young expanded the store into selling many different product lines. Young and local business owners Ferd Filger and Dr. Thomas M. Eagle led the incorporation of Riverside in 1951, after both Parkville and Kansas City expressed interest in annexing the area. As of 2015, the store was still owned by the Young family and was well-known around the Kansas City area for selling cheap beer, wine, cigarettes and gasoline.