I "ran" a good loop around Jefferson in the spirit of Mts Hood, St Helens, and Adams, which have standard loops. I did this in trail running shoes and no special gear, but the East side feels very mountaineerish below Whitewater. My sense from the total lack of cairns, bivy sites, etc. over there is that nobody really goes over there, but it is a great route that I think deserves some use from other trail runner types.
Main trip report is at https://medium.com/@jrit/mt-jefferson-high-loop-9c441b1ec586
Or if you just want to skip to caltopo for a track https://caltopo.com/m/MTC9T