Given the nature of your question I think the Road Trips forum is probably a better place to post:
I just don't see anything in this question that involves San Francisco (other than being the destination of the drive).
Hi, and welcome to TripAdvisor forums.
This page is about the lovely city of San Francisco. For your multi-state drive, I suggest either using the Road Trips forum or the Oregon state & California state forums. You might also glean useful information from the Oregon Coast forum.
You get to decide what is 'best.' Some folks might sample craft brews while others play with toddlers on a chilly beach or lounge at a romantic B&B. Your trip, your travel group, your travel style.
Road Trips: www.tripadvisor.com/ShowForum-g1-i12567
Early October can be busy in San Francisco as the weather is lovely and conventions are popular. Use the relevant topics in the Top Questions on the right side of this page to help you plan. (full TA website, not the app)
If the five days are just for the drive, I recommend that you go down the coast.
I’m grateful for all the replies. I have posted my question on the forums suggested.