Slitherboard

Take an ordinary skateboard and slice two inch wide gaps across its width at four even intervals.
Join the center of each segment back together again with either a thick spring or a fairly wide strip of high strength memory plastic and attach a set of trucks [link] and wheels to the underside center of each one.

I think that this would, not only allow the board to conform to varying surfaces but would also make for a skateboard that could be propelled, (once in motion) by the rider twisting their hips and then legs back and forth in an undulating scissor type motion, a slither if you will.
I think this may also let the outer rim of the board to be lit Piezo-electrically (not sure if that’s a word), for nighttime safety and of course coolness...wait scratch that, purple ground effects.


{Testimonial from my thirteen year old son}
"whauo that'd be totally sweet."