Oh my that is one of the most BEAUTIFUL drives you can make. Are you driving the coast? I highly recommend it! Be sure to take highway 1 not 101. It takes much longer to drive but this little two lane highway is well worth every minute! The views of the coast are amazing and it changes so dramatically from CA to OR. There are several things to see along the way.

Be sure to go to the Sea Lion Caves north of Florence OR. Oh my they really are amazing and depending on the time of year that you go, the "killer" whales will be up. The cave is just amazing and well the Sea Lions you can just watch for hours. This is one of the most amazing natural wonders that I have seen! Besides the Sea Lion Caves Florence OR is a very unique town. It still has its old town which is just like an old fishing village. A great place to eat there is ICM Restaurant right on the docks. They have the best seafood and run some all you can eat specials which are just cheap! The area around Florence is just amazing! They have plenty of fishing, hunting, camping, hiking and more! It is just a great place to stay and explore nature!

Bodega Bay, I don’t know if you have been here before but, when I travel I love to see quirky stuff, well "The Birds" by Alfred Hitchcock were filmed here and there is a place called the Tides Wharf Restaurant (part of the tides resort) they shot the "bar" scene here along with several other shots. Very nice place to eat, wonderful food and a great history. The whole place is decorated with prints from the movie, pictures and posters. You can just go in and see the market and the memorable. Also right there next to the restaurant is the dock that was used in several shots. You remember where she takes off to the island well this is where it happened. You can even get a guide book that will show you were parts of the film were shot. I thought it was pretty interesting and something different.
http://www.bodegabay.com/features/birds.html
http://www.innatthetides.com/

If you like to camp and want some really good time in the Redwoods I recommend Fort Bragg. I was surprised by this little town. First of all we found some of the best camping around; we were able to camp on the beach and also in the Redwoods. There are several state parks nearby that offer great hiking trails and more!
http://www.fortbragg.com/index.php
You also get amazing whale watching experiences depending on the time of year you go. There are several places to pull over on the road and take a look, again most of the state parks have viewing areas. You can also take a whale watching cruise from here. The whales are just amazing!
For camping in Fort Bragg we really enjoyed the Wildwood Campground which is in the forest or Harbor RV Park.

Another fun quirky thing to do is Tour Thru the Tree located outside of Klamath CA. Unlike other drive thru trees this one is thru a Redwood, if you have an extra large vehicle beware!! The great thing about this place is yes while you have to pay money they do have a spot by the tree to park, they also have a picnic table, have some lunch or a snack and watch other try to guide themselves through the tree. We had a lot of fun doing it and trying to watch people get through!
http://www.klamathcc.org/home.cfm?dir_cat=37883

The Trees of Mystery in Klamath are also pretty cool, again another different roadside attraction. First of all they have a wonderful Native American Museum here, one of the largest private collections in the US. Second they have some great hiking trails. Third they have gondola rides through the trees, some call them tram rides ect.. You still get the most amazing views of the Redwoods and the surrounding landscape!
http://www.treesofmystery.net/entertain.htm
http://www.treesofmystery.net/museum.htm

Ocean World in Cresent City is really neat. Located in an old ship they have a wonderful private aquarium. The stars of the place are their two rescue Sea Lions and a rescue Harbor Seal. All of them are amazing and put on quite a show for you! They also give you the chance to pet a leopard shark. If you have never had the chance to do this it really is cool! This is not the Monterey Bay aquarium and the tour only takes about an hour, but it really is a lot of fun, and another crazy roadside attraction!
http://www.delnorte.org/
This whole part of the coast is just amazing the Redwoods meet the sea here and the drive on the PCH is just amazing winding along the coast and then into the Redwoods it really is a wonderful drive! There are also several state parks in the area that offer wonderful hiking trails of all lengths. Not only do you get to see the beautiful forest but, you get to see the wonderful coastline.

I don’t know if you have been to San Jose or not but I suggest a stop at the Winchester house. This place is just crazy! It is said to be haunted, we didn’t see any ghost but, we were amazed at what Sarah Winchester had done with her home. The Winchester House is truly a rarity here and I loved every minute of it!
http://www.winchestermysteryhouse.com/

There are tons of places that I would recommend in OR. Be sure to check out Crater Lake. This place is just awesome! There are several places to stay in the area, and the parks around here are just amazing! Crater Lake National Park really has a lot to offer for the outdoors person. There are plenty of hiking trails and nature is just abundant here! We try to visit Crater Lake often for a relaxing time. I would defiantly make time to stop here!
http://www.nps.gov/crla/

Another quirky thing is head up to Astoria OR. This town is just awesome and you have seen sites from here in movies. Be sure to take a movie tour, we found this very interesting! There are also wonderful places to view the whales and great places to enjoy the outdoors. There are few places like Astoria left; we just found this place to be a little gem!
http://www.oldoregon.com/

Be sure to check out Portland. I love Portland it is such a unique place. This city is growing and is very amazing. There is a ton to do here from museums to entertainment. There are plenty of places to stroll and shop and downtown is just cool to see, you never know what you will stumble upon. They have wonderful places to dine and a great nightlife.

Another interesting place is Cannon Beach OR. The beaches here are just amazing and there are plenty of outdoor activities to do. We love to horseback ride here, what a great way to experience nature. There are several beaches here that you can walk on and be alone; again this is a wonderful place to view the whales! Haystack Rock is located here and it truly is a sight to see. There is a wonderful trail that is very short and gives you great views of the rocks and the coast. There are also several viewing areas that you can pull off the road and just stop and look! Wonderful this place is amazing!
http://www.ci.cannon-beach.or.us/~Natural/hrap.html
http://www.cannonbeach.org/nature.html

There is a ton to see on your journey here are some websites to research it more:
http://www.us-101.com/
http://www.traveloregon.com/
http://www.roadsideamerica.com/

Weather wise I would plan for COOL temps, bring short sleeves and pants but I would also bring long sleeves, sweaters, sweatshirts ect. You want to dress for windy conditions and cool temps. Bring a jacket!!! If you are from SF the northern weather should be no surprise to you! Sunglasses are always a must, even though it is fall here, the sun still reflects off the water! You will also get to see some great changes in the forest, nature will not disappoint you!

Have a great trip I hope this helps!

Mt. Shasta was nice in January for skiing; I don’t think that’s available in Oct.

If you’re driving along Hwy 5, stop in Weed and pick up a t-shirt. Otherwise, I’ve heard the PCH is a nice ride.