I neither race nor organize anything, so I’m just throwing out ideas for others to consume and do with what they will.
Behold: the Pittsburgh Alleycat Cyclocross race.
I believe Pittsburgh’s “stairs with a street name” are a fairly unique urban feature. The Pittsburgh alleycat cross race would find an area with a high concentration of named (public) stairways, and use these for the mandatory dismount portions of the cross race.
Sort of a life-sized version of Chutes and Ladders, perhaps?
Anyway, sorry if this has already been done here or elsewhere, but it sounded good when it occurred to me.