A long time ago I made a thread about how I recorded my kayak trips this way. I would make a folder for each trip and use the Line and Placemarker tools to draw the path of my kayak and place icons for points of interest (where I disembarked, etc.) as well as logging weather, time of departure/return, and what happened during the trip. I also placed Camera placemarkers where I took pictures along the trip, adding as notes the name of the picture file and when the picture was taken. I gave every line its own colours so that I could tell them from one another when viewing all of them at once.
You grow tired of it eventually, but before you do you have a great image on your Google Maps of a set of lines in all kinds of nuances of blue and green showing
a lot of trips. It's quite a cool thing to see, actually.
Here's the thread. Features a more in-depth explanation and a screenie of my kayak log in an early stage. I lost most of it due to a HD crash, but I know I have a good chunk of it backed up to my hotmail account... somewhere

. At least... I hope it's still there, haven't found it so far.
This new feature is incredibly cool, as a matter of fact I once wished SH games had this feature, but thought it too much to hope for. Heh, maybe they got the idea from my thread :p .