Mike, you're a Minnesotan, were (are) you a hockey player? IIRC, the skate companies make hockey-style inline models. I've also seen inline hockey leagues, which might be an acceptably non-doofus way to participate. [Disclaimer: I used to play hockey, but have never tried online skates.]
Bike/fitness trails seem like reasonable sites. I've even seen X-C ski type roller setups with poles, which were interesting.
One caution: I know of a dude, ex-hockey player and decent athlete, who fell down on his first day of online skating and broke his wrist in 8 places. So I'd suggest purchasing protective equipment, certainly knee and wrist guards...