Movember in Norwich

I was thinking reveal all the checkpoints at the start, make it more about the riding and routefinding than map-reading and searching - but actually that sounds like a pretty good idea. Give each team a random first checkpoint, then the marshall at that point writes down their arrival time and tells them where the next point is..

If you're going to reveal one checkpoint at a time then you'd need to send everyone to them in the same order, or else each team will have a completely different prescribed route and distance to ride. Some could end up being sent back and forth across the city while others get lucky and are given a quick circular route.

But, the trouble with a true point-to-point race is heavy bunching at the start and also everyone just following the leader, so you'd need something to string the pack out before the first checkpoint. This could be achieved by making it a long way off, putting hills in the way, making it hard to find, having a staggered start like a time trial, etc. I'd favour the first two, if anything. Though a staggered start could be interesting, then you could offer the checkpoints AND the order in which to visit them. But, then you lose the bustle and chase of a mass-start.
Lots of ways to do it, I guess.

I guess in this case you could give all the checkpoints upfront and also offer a tip that an optimal route describes a moustache shape across the city - that will make people think carefully about where each of the checkpoints actually is in the city and try to plot a route before setting off.