I don't know if it's like this for all or most clubs, but the IAR routes are picked so that the shortest distance is generally between controls. So there's no good way to cheat short of hopping in a car.
As for the OP, I think that keeping the route well-defined and shared in advance, yet informal (a bunch of friends getting together to ride bikes, IOW) would be the best way to start. You may have to worry about liability and insurance and that kind of thing if you make it too big and official.