First one I'll count as a tour was a two day 134 mile ride from Boston to tip of Cape Cod. I organized this ride for some friends while in college. My bike wasn't in the best mechanical shape, but I could usually stop myself by dragging my feet. Things went wrong about 10 miles into the ride while riding a trail through a local park. The route went down a small hill and around a bend. I made the hill but missed the bend. My bike stopped and I somersaulted over the handle bars. I landed on my back, mostly ok but on lower right scraped up against a rock.

It would have been reasonable for me to go home at that point. However, I was young, male and invincible. Since I was the leader, there wasn't anyone else to send me home. We bought some 3x3 bandages from nearby pharmacy and taped up the wound. I toughed it out, but it hurt a lot, particularly later as sweat got into the wound. It was quite hot, and I nearly bonked except for getting some bananas not far from the bridge onto the Cape. We didn't get quite as far as we hoped and so as it was getting dark we asked and then camped on lawn of a church in Barnstable. A friend helped change the dressing on the wound. Next morning we were up early and rode the rest of the way to P-town. On completing the ride and cycling through downtown Boston to home, I beamed with accomplishment at having made the ride (even if in hindsight it wasn't the wisest choice).

The "wrong" part is an easy lesson about making sure your brakes work. After that ride, I continued with a steady progression of further weekend, multi-day, week-long and longer duration rides up to 12 months long. I'm still learning as I go along...