Snow is possible, but unlikely
George,
While snow is always possible in late October, it is pretty unlikely. US-199 has a couple of rough spots (narrow lanes) and plenty of truck traffic, so take it easy in any weather condition.
The best guide we have ever seen for really unique and fun restaurants is the one by <a href = "http://www.roadtripamerica.com/read/California-Highway-1.htm">Lonely Planet<a/>.
One of my favorite inns in the world is in Mendocino -- the <a href = "http://www.roadtripamerica.com/places/stanford.htm">Stanford Inn<a/> on the Big River. I don't suppose that Rockaway, Oregon is far enough for your first stop, but a recent post on the forum described the <a href = "http://www.roadtripamerica.com/roadtripamericaConference/Thread.cfm?CFApp=44&Thread_ID=2862&mc=1">The Beach Stay<a/>.
Hope this starts the process for you.
mark