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Big Sur

if you take the 101 everything will be prettier

You could see the Tillamook cheese factory, natural bridges near brookings, fern canyon in redwood national park, drive along the avenue of the giants, stop in fort bragg for the glass beach, stop in SF (land's end is a small but gorgeous area), and then go to santa cruz/monterrey/santa barbara if you want

If you take the 5, eugene raptor center/natl history museum + looking at mt shasta, and then you could stop by SF if you want

Hit up crescent City and the redwoods all along 101. Prairie Creek is a chill park with some great day trails

To clarify on the folks suggesting US-101, take SR-1 which is along the coast the entire time. US-101 and SR-1 are the same road most of the time, but US-101 will split off into metropolitan areas as it's the actual arterial highway people use. SR-1 is the scenic version.

Mt Shasta / Weed

You could stop at the redwoods. Take a stop at Patrick’s Point (look up photos if you want). Arcata is one of my favorite north California towns and is just kinda good vibes. There’s a place there that does savory pies that I’ll stop at if I’m ever on a road trip. You can probably find an oystery on the way down too if you wanna do that but if you live in Portland buying some cheap oysters direct probably isn’t that amazing.

I think there’s a nice hard cider spot in eureka you can stop at and buy some jugs from for later if you like cider. That’s about it for stuff I’d stop at if I was doing the trip

Definitely see the redwoods if you never have. Or even if you already have.

Highway 101 goes through Humboldt County, home of Redwoods/Sequoias. There is a small road off the 101 called Avenue of the Giants that follows 101 but is a small two-lane road that weaves through the trees. It's pretty awesome! The 101 is a little longer, time wise, than the 5, but I find its more scenic.

Whatever you do, don’t try to squeeze too much in. Find one nice thing and do that.

Like others are saying, Avenue of the Giants, it's right along 101, not even a major detour, you don't have to stop, just drive through and take it all in

Mt Tamalpais, you can get a nice view of the Marin headlands, SF, and the bay, it's satisfying if you like peaceful mountaintops dotted with observatories

Golden Gate Park, Academy of Sciences, De Young, Legion of honor.. these are pretty expensive but walking around there is free and pleasant. Land's End. Ocean Beach. Lunch in Pacifica, Monterey, or farther south, depending on where you end up

Stick to CA-1 wherever possible, 101 otherwise

Come through my town and give me a high five, lol, fr though

Highway 101 > I-5

Mendocino is a super pretty town. Drive big sur between SF and LA. Epic drive. The henry miller memorial library is a cool stop.

Adding to the voices saying ya gotta stop at Prairie Creek redwoods State Park. The nearby town of Arcadia is kinda neat too.

Mt. Lassen National Park, 2 hours east of redding. One of the only active volcanos in the lower 48

Take a detour up to Seattle and play some music under the three level elevated highway next to the aquarium. Great acoustics.

One time I nearly fell out of a roller coaster at Enchanted Forest ( 8462 Enchanted Way SE, Turner, OR 97392 ) as a kid

Great suggestions for CA but I’ll throw out Carlsbad caverns for when you’re further along in the drive.