My most memorable drive was probably this past spring when I drove my car out to the Boston area in March, put another 10K miles on over the next three months doing work and then returned home only to turn around and drive down to Indy for work training and home again a few days later. The interesting and memorable part is that my front shocks were shot, and I was able to find someone out in Boston to put new ones in for me privately for about $300 all in, and that although i didn't know it at the time, I had a partially blown head gasket and leaking oil pan gasket. I kept up on oil fills, the car ran fine for the most part and never let me down.
Otherwise, nearly every work trip is a memorable one. I'm an insurance claims adjuster and have to carry a 17' ladder with me most of the time which I strap onto a trunk mounted bicycle rack. It does the job, and I usually get a comment about it nearly everywhere I stop. I sometimes think that I should sell this car or trade for an E34 or E32 for a little more room. A hard roof car would probably be a better year round car for what I do, but this one sure makes the trip interesting.