I-5 is easy traveling (except for high-traffic metro areas) up to Olympia. (I’ll let someone with more experience chime in on Teton Pass and the Grapevine). You won’t hit mountains until you get to Redding, Ca, but there’s nothing crazy. Various grades from about the California-Oregon border to about Eugene. As for weather, December can be sunny and mild or stormy and snowy. It all depends on what’s coming through. It takes a pretty good storm to force chain restrictions on the passes near California-Oregon. It happens a couple of times a winter on average. Get a good weather app and bookmark the Caltrans Quickmap for all road conditions. Same for Oregon and Washington. I’ve only driven cars through Portland and Seattle, but wouldn’t want to tow a trailer through those during rush hours. I’d suggest timing it to avoid those periods if possible.
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1999 Ford F-250 Super Duty Lariat SC, 7.3L PSD, 3.73
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