Curious to find out what everyone has encountered while trying to camp or "stealth camp" while going on a multi day ride. whenever I've camped while riding its been a controlled situation. Just curious as to others experiences on the subject. it dosent necessarily need to be in chicago, i mean like going out west to like starved rock area or north to beach state park.

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I've stealth camped a lot while hiking, and to a much lesser extent while touring. But in both cases, I was never anywhere remotely urban or suburban. In general, here are the things I try to remember:

Leave no trace - This is a good policy to keep in general, but goes doubly so if you're camping somewhere that isn't friendly towards camping. 

Be Respectful - Of people you may encounter and of their property. They're less likely to be mad at you if you're polite and cooperative.

Stay away from the road - Or trail. Whatever. Make sure you're off the sight line, both so as not to disturb others and not to draw attention from the people who might get mad at you. A earth-tone tent/tarp helps. You don't need to go camo, but avoiding day-glo is a good idea.

Don't spend more tine than necessary - Pitch camp after food, sleep, break camp, then do other things. Your camp should exist for the least amount of time possible.

Stay off private land - This isn't always possible, but is a good idea.

I've never run into any real trouble, although once I ran into a property owner when I was inadvertently camping on a section of his land. I left when asked and was polite, and we had a nice chat. I moved a mile down the path, re-pitched, and slept the night. Stealth camping is a good way to go places without having to plan a route, but I'd want to be a long way from anywhere here before I did it.

I've never had any problems result and have stealth camped in various places around the country while cycling.  Usually, I don't plan to, but for whatever reason, am behind schedule and can't reach a campground or hotel.  Finding a discreet location at the end of the day is the secret.  Set up late, leave early and Leave No Trace behind is the best policy.

Marc 

Back when I did it somewhat frequently, I was glad to have a dark green (mostly) tent.

It can be a lot of fun, but also nerve-wracking and of course it happens at the time of the day when one may have a pretty low reserve of emotional strength. As Jeremy and Marc note, you want to set up camp late - ideally without much (or any) daylight left for obvious stealth-related reasons. But actually finding a viable spot and setting up even a simple site in the dark is not fun. Using lights also undermines ones ability to stay concealed. 

You have a great advantage being on a bike - you can probably get a lot further from the road than most anyone doing a night patrol is going to bother to look. 

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