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Steve Roper in his 1976 book The Climber's Guide to the High Sierra describes Shepherd Pass as "... one of the more dreadful east-side approaches in the range. The ascent from desert to alpine zone is an interminable ordeal of dryness and steepness. A five hundred foot decent midway is a classic destroyer of morale, regardless of direction one is traveling."
Although this description is factually correct, something about this pass continually draws me back (as of 2019 a total of 8 times - to be fair only 6 of those times did I actually cross the pass). However, I have crossed Shepherd 2 additional times by way of Junction Pass. Until the completion of Forester Pass in 1932, the Muir trail crossed to the east side of the crest via Junction Pass and the recrossed to the west side via Shepherd Pass.
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Shepherd Pass-Slide Show