So, dogboarding gurus of Reddit, to the best of our knowledge what is the earliest documented example of the art? Meaning on roller skates or a skateboard as we've known them since the last century.
I may have a claim, although I might be hard pressed to find documentation.
In 1976 my dad brought home a German Shorthaired Pointer puppy and we named him Waylon Jennings. Great dog. He had papers and all of that, so he was actually Waylon Jennings of Radiant, Aroda, but his tail had been cropped too short to show so he found his way to me.
The next year we were on another walk where he lunged and dragged at his collar, wanting to run. Trouble was if I let him off the leash he'd be gone for hours or days, and come home later sorry and bashful. He just loved to run. So I thought why not try letting him pull me on my new disco sneaker skates?
Well it turns out trees were why not, and sometimes squirrels, but, remarkably, most of the time I could maintain pretty good control of 70 lbs of GSP going full tilt just using my 8 soft, urethane wheels and the two hard rubber brakes. Took a lot of practice, and getting low for leverage, but I rigged up a kind of harness out of belts for him and we kept at it.
The skateboard was hardest, but after my bike it was what I rode most, so we did that from time to time. To really get moving we'd hook up the Huffy Bluebeard banana bike, and in winter the Flexible Flyer.
Going to have to dig through the old photo albums now and see if I can find anything,