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I don't think that's stupid at all. You chances of getting robbed on the TransAm are probably less than one in a thousand,
In small-town churches nowadays, the pastor is more likely to be a she.
Quite often, the church sign will have the pastor's name.
Sometimes, they have multiple churches they serve in a few nearby towns.
It's easiest to ask - "Does Rev. Smith live here in Smallville?"
If she lives 30 miles away - then ask if a minister does live in Smallville.
So, the Baptist minister - Rev. Johnson - lives over on Maple Street.
So you call Rev. Johnson, instead, and ask. Don't expect.
But you will usually be pleasantly surprised by the generosity.
As for public lands - I find the purchase of National Forest maps worth it.
They show surface ownership patterns - with a scale of 1 inch = 2 miles.
So they are pretty detailed for touring and back roads, too.
They have them in paper ($5) and plastic ($10). Or thereabouts.
Even one night of pricey camping more than covers the cost of a plastic map.
Most larger towns near forests have a Forest Service office.
Plus, town libraries will often have areas maps, too.
A plan to stretch the ride over 3-4 months.
Another option is to ask at churches. Liability issues have made churches more squeamish, but the pastor may allow you to camp out back and use the facilities.
The most widespread free camping is on federal lands. You can camp for free on almost all Forest Service and BLM land - but you need to know where it is. Most is in the West - but there are national forests all over the U.S. This does NOT apply to National Park and National Wildlife Refuge lands - where random camping is prohibited. Most states lease state lands to ranchers or other users so random camping is not allowed. Some states DO allow camping at fishing access sites and on state game lands. Finally, don't random camp on Indian Reservation lands.
I'm considering a long distance trip this summer, biking from Orlando to upstate NY. I don't have any riding partners so I'd be taking this alone. Am I crazy and stupid? LOL, but seriously I'd like to here from anyone else who has done a cycling trip alone and hear their experiences and words of wisdom.