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how did he skate up and over the Rockies?
He kick flipped real hard
He kicked the mountains and then flipped them off, they felt so disrespected they moved north and waited until he had passed them.
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.