Andy: most Saturday mornings over the past 6+ years I lead a ride from my shop, 
Hiawatha Cyclery in Minneapolis, that is much like this. The route is 
determined on the fly and there are often offroad stretches and various 
obstacles to surmount on the way to/from breakfast. At the beginning of each 
ride, I usually have only a vague idea, if any, where we're gonna go. We have a 
few regulars who are confirmed "roadies", and they sometimes defect when the 
deviations-from-boring become too much. Amazingly to me, rides that have the 
same (usually dull) route every week seem to be wildly popular, while an 
unpredictable but fun ride puts people off (because I can't give them a 
straight answer about distance, speed, or other meaningless stats). Anyway, it 
sounds like your ride leader and I are on the same page! It's so easy to get 
into the rut of commuting everyday and having only a tiny number of 
recreational loops to ride. But the permutations of adventure in any major city 
(or elsewhere) are endless.

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