What was a "rolling road" and what did it have to do with tobacco?

 

Back in colonial America, tobacco was tightly packed in large barrels, known as hogsheads, for shipment to market. The hogsheads were not placed on wagons, instead they were outfitted with an axle through the middle and literally rolled to market. These market trails were called rolling roads.
If there's a Rolling Road near you, that's probably how it got its name.