Here is a detailed description http://www.everytrail.com/guide/skyline-to-the-sea-trail. I hiked it a few years ago from the Long Ridge OSP, and some people start by going up the Black Mountain. These options bypass the trail along the hwy 9 and hwy 236, which can get noisy. My daughter hiked this year from the Castle Rock and did not like the part along the hwy.
I did this trail 3 weeks ago. Castle rock was really nice and you can avoid much of the roadside hiking by taking the old toll road instead of the skyline trail until just after watermans gap.
Have fun and remember that there is beer and food at big basin.
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