had one of those little plastic boards when I was a kid. there was a condo complex up the street with a lot of long, squiggly sidewalks to cruise, and some shallow stairs to float down.
never owned a longboard. but used to do a little bit of it on my Santa Cruz shortboard. I'd picked it up during my early post-divorce wild days when I was stuck in Leander with no money and nothing to do but fish, mtb, and take naps.
anyway, there's a street forming the northern boundary of Walnut Creek Park with a big hill. I used to carve my way down that until I just had too much speed to hold the turns (sliding just didn't seem like a great idea), and would take the last hundred feet or so just straight down. it would bottom out and go back uphill to a dead end to slow back down. just the perfect spot for that sort of thing.
my neighborhood had one hill, at the very back. pretty mellow; but on a skateboard, it was plenty fast. about 6 turns I could rail all the way to my house where I'd just bail out onto the grass.
went out to Ramp Ranch on 29 some, back then. learned to drop in there and play in the 1/4 pipes. got put on a project out in Sunnyvale, discovered a real skatepark near my hotel, and got better. shortly after that, Austin built its first concrete park down by the IRS. would get there right at sun-up, before all the kids woke up. couple times, there was another old guy there sweeping and skating the pool in the dark with some cheap little LEDs clipped to the bill of his ballcap. fuckin crazy. good skater, tho.
now all I do is ticktock up and carve down my longish, curvy driveway. good core workout. lotta fun, esp for the investment.