Oh dear god, I finally cleared my schedule enough for dinner at Reo's (actually, I got an obscene quantity of takeout, hit Target for a cooler to pack it in, and high-tailed it to the beach). What a revelation. Although I was only moderately impressed by the beef ribs (Czaba's on Lombard in North Portland has this really unusual sauce with elements of apricot and orange, which sounds heretical, but really sets off the smoke), I was Completely Blown Away by the brisket. It is nearly the equal of the TX Hill Country's finest. The sides were also ambrosial. The pork ribs and chicken were also excellent; the best I've had in the Pacific Northwest, by far. For those who didn't read the review yet, it's at 175th and TV Highway in "Aloha", an unincorporated area of Washington County between Beaverton and Hillsboro. This is the place in the reviews that is most worthy of a detour of any of the places in Oregon; I cannot repeat how good this BBQ is.
I feel compelled to comment about Chives. I've known Chives since 1997-98, when they were in Brookings. I've had great meals there, and I've nearly walked out. The service is at best adequate, and sometimes descends to the near-snarly. The prices are high for the area, the attitude can at times be a bit pretentious, and I'm Just Not A Fan. It's not Roadfood(tm). I haven't been there since the move to Gold Beach - and I really don't have any urge to. Chives is an attempt by Curry County Hillbillies to put on airs.
More Roadfoodish, and with wallpaper that is worth the drive, is O'Holleran's Steakhouse on the north end of Brookings. The beef isn't anything spectacular; it's just a good place to have dinner. Lots of people celebrate special ocassions here. They do the relish tray/soup/salad/ice cream thing with every meal, and the servers are career waitresses usually. I feel like a Manhattan every time I walk in there. Make sure to note the wallpaper in the bar; it is priceless.
It's really sad that the south coast is such a pit of despair when it comes to fine dining or even honest midmarket dining. While there's not a proliferation of chains (the tourist trade is so seasonal, and the populations are pretty small), there's a lot of indifferent food being slung by people who don't seem to give a damn anymore. Service is universally incredibly bad, in large part because young people who haven't been outside the area don't know what good service is suppossed to be.
Sorry if this sounds like a rant; the Oregon Coast has some of the most amazing seafood of anywhere on the planet, and it's possible to have a very close relationship with not only your fishmonger, but also your fisherman. If you're RVing or have some way to cook what you find, you can be blown away by the total freshness and care in handling that these hard-working people are providing.
Further up the coast, the food tends to be better, by virtue of being closer to the farming areas of the Willamette Valley (better produce) and the year-round business provided by being close enough to the Portland area to be a comfortable daytrip.
Noting the route of the original poster, if you're going to be at Crater Lake, you might as well come back via the scenic North Umpqua Highway and plan to have dinner at Steamboat Inn. It's exceptional; fresh Northwest cuisine, served family-style at a beautiful fir table in a fishing lodge right by the river. It's memorable. Their URL is http://www.thesteamboatinn.com
, and reservations are essential.