I see skateboarders carrying their boards on bike all the time, but usually they're slung crosswise over the handlebars or the rear rack, which is both aesthetically jarring and potentially dangerous (the handlebar version, at least). A much better solution for this admittedly specialist problem is the Fairdale Pannier Skaterack, a special skateboard carrier which velcroes into place on your existing rack.
The lightweight carrier has a loop into which you hook one truck, and a bungee cord up top to keep the whole thing in place. The board is positioned back behind the bike's rear axle, so you can't hit the board with your heel as you pedal.
It's ingenious, and more flexible than Fairdale's original design which comprised of a full rack with the skate carrier built in. Price and shipping date are not yet finalized.
Skateboard Rack [Fairdale via Prolly]
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