In the 90's a band named Fifteen was playing in Philadelphia with a band named Propaghandi. They were set to play some dump in philly that is now defunct, but was a legendary show space named the Stalag 13.
Anyway,Jason Angst (who is now like one of the best tattoo guys ever or something, click the link..) and I loaded up our overloaded road bikes with not enough stuff, no rain gear, backpacks, and a Delorme atlas. The plan was to ride to the Poconos so I could make out with a girl for a few days, then head down to Philly. Total of about 450 miles or so. Easy enough.
The first day was 70 miles in cold pouring rain. I think this was pretty defeating. We slept on the side of the road in the tent and froze. I just had a small blanket and we were in the Appalachian mountains. No ground pad. No sleeping bag. I remember just laying on the ground waiting for daybreak to pack up and try to warm up.
We rode the next few days, one of which was my first 100 mile day. It was exciting. We got to where we were going, and within a day my body shut down. I had some sort of fever, cold, exhaustion. Jason went down to philly without me. My romantic teenage plans of making out with a girl nonstop were turned into her making me soup and tea.
I missed the show and the band doesnt play anymore. I still love them. I am glad that my first bike touring experience didnt scare me away from doing all the subsequent tours, cause they have been some of the best times of my life.