Ah, it is now early November, and Bend weather is in glorious full-on sucky mode -- cloudy, gray, cold, drizzly, gloomy. It will stay like this until mid-June or so.
We typically get a break in the sucktacular weather in mid-February, which fools all the locals into thinking it's Spring so they break out the shorts and T-shirts and Birks. And then The Endless Bend Winter clamps down again.
I have found the best way to deal with Bend's sucky winter is to not fight it or deny it. Stop pretending that this is The Oregon Sunbelt. (Well, actually it is -- but that's like saying someplace is "The Siberian Banana Belt.") Coccoon with a cheerful fire, lots of good books, music, DVDs, video games or whatever's your pleasure, and wait for the arrival of Spring. (It WILL get here eventually, trust me.)
What's really aggravating are the nimrods who try to pretend that Bend's winter isn't sucky, or -- even worse -- that they LIKE cold, gray, dreary, drizzly, dismal weather. NOBODY likes that kind of weather. Anybody who says he does is lying to you or to himself or both.