My "personal best" was in the BWCA on my first trip.  There were six of us, three young uns' and three mature types.  I was carrying a Spirit II and coming to the end of the portage.  I noticed a log laying out into the water.  The three young uns' were just dropping their loads and waiting for me so they could start loading. I thought I'd just walk out on the log and "flip" the canoe into the water.  I made it out onto the log OK but when I went to "flip" the boat my foot slipped and we went in together, boat on top.  After I crawled out and did an inventory of hurts (arm, leg, head, hand, etc)  I happen to notice the three young uns' laughing their butts off!  I should have charged them for the entertainment!   >:(

My scariest one was not portaging but loading my Roylex onto my car top.  My wife and I had just completed a multi day trip down the Nabakagon and St. Croix Rivers.  We were at a very nice boat launch complete with concrete ramp.  How good does that get?  Anyway, as I was going around the vehicle to get into position to put the beast on top the car I moved sideways for clearance.  My foot hit a rock and I tipped over away from the car.  The boat went flying but as I fell my head hit a large rock on the way down.  Day turned to night briefly as the stars came out and danced around for a few seconds.  My wife, the nurse, kept asking me if I was OK.  I said "of course".  She later told me that one eye was pointed one way and the other another way!  If that rock had been pointed rather than round I probably wouldn't be typing this.  :-/