My guess is that hitchhiking+skateboarding means grabbing an actual moving trailer hitch or three. Were he manually kicking the pavement with zero assistance, I cannot imagine covering 55 miles a day without it being downhill the entire time. After all, it is F L A T after you cross the Rockies. For at least a thousand miles. That or he has legs like tree trunks.
My guess is that hitchhiking+skateboarding means grabbing an actual moving trailer hitch or three. Were he manually kicking the pavement with zero assistance, I cannot imagine covering 55 miles a day without it being downhill the entire time. After all, it is F L A T after you cross the Rockies. For at least a thousand miles. That or he has legs like tree trunks.