Depends, as you said, during this time the weekends are packed. I would book if doing things on weekend. For me I can sleep outside in a park bench. Some people might be different
I ride till about noon, look at a map and figure where I want to be at quitting time. Then I book a room.
a memory for you
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I just park whereever. I've been known to forget my keys in my bikes, too. lolI've never taken my bike on an overnight trip, do people usually bring a disc lock or use an alarm when they park overnight?
I've also found some gems with Trip Advisor, in budget motel brands