You're coming close to describing local figure-8 racing. Ever seen it? Our local track, Orlando Speed World (everything in Orlando is "something world" - Disney World, Sea World, Citrus World, Seashell World, Bargain World, But I Digress World . . .)
Any way. A few times a year we have figure-8 school bus races and figure-8 trailer races. The trailer races are with cars puling trailers. The have to cross traffic in the middle of the track Sicne it's often the camper trailers that get hit and not the cars, the cars end up dragging around trailers that have tipped over and are shedding bits of their sheet metal. It's wonderful fun. The school bus races are a big hit with the kids. Bill Geist on the CBS show Sunday Morning did an article on Orlando Speed World and the figure-8 racing.