When I hiked the Florida Trail I carried an amateurishly published thru-hikers guide book.  I called it the “Hobo Handbook” because so much of the time the logistics it suggested were dependent of the kindness of strangers.    In one town, the guide book said if you check in with the sheriff he would let you sleep in the park.
First I went to the post office.  I was receiving my big bounce box that had all my maps, trail info, fuel, and other supplies in it.   It was a large plastic bin.   I was also receiving some other gear and had a pair of shoes I needed to send in for repair.
I gathered my boxes from the post office and sat down under a tree. While I was getting things organized and sorted, the post office closed.
I put on my pack, gathered up my big plastic bin and other boxes, and walked to the sheriff station.
I was sick, tired, dirty, and my feet hurt but I smiled, acted enthusiastic, introduced myself, and said, “I’m hiking from Tampa to Maine.  In my guide book it says if I check in with the Sheriff I could sleep in your park for the night.”  (big smile)
The guy looked at me with a deadpan expression and yells into the next room. “Ed, Ed…..come here and look at this.”   Ed comes out and he continues, “She says she is hiking to Maine and wants to sleep in our park.”    They look me up and down for awhile and smirk the way law enforcement does sometimes, and I’m realizing that they are not seeing the intrepid adventurer I was hoping to project but some dirty stinking homeless woman caring all her possessions in a big plastic bin.
“You say you read this in a book? Let’s see the book. ”
I unfold an 8.5 x11 piece of paper from my pocket and hand it to them.
“I thought you said it was a book, this isn’t a book.”
“I only carry the page I need for the day, The rest of the book is in my resupply box.” I pointed at the plastic bin.
“This doesn’t look like a page from a book.”
“Only a few people buy the book so it’s just a self published thing.”
He looks me up and down and then says, “I don’t suppose you have any ID, do you?”
“Well, yeah. I have a drivers license.”
He tells me to slide it to the guy behind the glass.  Then they run a check on me. After awhile he says, “Well I guess it would be alright.”
I smile, thank them, and then I say, “Hey, the post office closed before I could send my stuff on.   Could I leave my bin and boxes here until morning?”
“Oh, no! Come tomorrow morning you’ll say there is a million dollars missing from those boxes!”
So I pickup everything and head to the park.
In the park, I’m not sure how comfortable I’m allowed to make myself so I don’t set up my tent.  I lay my boxes all around me, unfolded my pad and lay down.  It was still daylight and there were kids with their parents in the park.  The parents looked at me suspiciously and sheltered their little ones from me.
At night I had coughing fits and I woke to a woman holding a cell phone shouting, “Ma’am, Ma’am are you all right?”
“Yes, I’m hiking the Florida Trail and I got permission to sleep in the park from the Sheriff.”
“Well, that’s who I’m on the phone to right now.” she said.
Stuff happened all night in that park but about 3am the strangest thing happened. I heard a car door slam.  I opened my eyes to see a big man walk like a stiffed leg guard up this pier. Then he got down on one knee and stayed that way for awhile. Then he stood up and did that same straight leg walk back to his car and drove away.
The next morning I got everything mailed and hiked on.
It’s hard to be sick on the road but sick on the road with unfriendly people and the world becomes a big and lonely place.  Now I carry antibiotics because when I’m sick it’s so hard to have the energy to find a doctor and a pharmacy in a strange place.