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I may be bringing an enclosed trailer from Northern California in December. I would prefer not to take I-5 up the Grapevine. Not planning on doing anything if it snows. 2004 2WD regular cab F150, V-6, auto, 3.55 open diff, 193 thousand miles. Trailer probably about 2 thousand pounds unloaded. I'll probably stop by a CAT scale to get an accurate number. Planning on adding a trailer brake controller before then. No towing package on the truck, but Ford didn't include an aux trans cooler for V-6s even with the towing package. But I added trans temp and diff temp gauges, so I can at least keep an eye on them.
I've driven up the Grapevine many times from the Central Valley to LA. Never with a trailer, though. And I don't tow regularly, probably U-Hauls ten times of less since I got the truck.
How much easier is I-58 through Tehachapi than I-5 through the Tejon Pass? I am assuming wind is not a factor, but I know that changes every day. I'd probably take 14 back down to the I-5 to return to LA rather than the Cajon Pass.
Alternatively, how is California 166 through McKittrick to the 101? Other than the Buellton to Refugio downhill and the Camarillo grade, 101 seems like it should not be a challenge. But I've never taken 166 all the way from the I-5 to the 101.
58 is divided and better than 166 but fwiw I'd stick with I5. The hill section isn't that long. You can tuck in behind a slow big rig and make it easy on your engine.
58 will have some hills to climb as well and is the long way around the short problem of the grapevine.