I'd give the nod to the Banks-to-Vernonia Trail over a ride to Astoria.
Some great places to taste beer right in the heart of downtown: Rogue, Deschutes, Bridgeport, is 10 Barrel open yet? I'm not as familiar with the eastside, but Apex was pretty cool.
Hood River to Rowena Crest and back is a great ride that my wife and I do together.
I'd also skip the Willamette Valley as a full trail - but there are some nice parts for sure.
Bend is worth it and the cycling and breweries measure up nicely.
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"The older you do get, the more rules they're gonna try to get you to follow. You just gotta keep livin', man, L-I-V-I-N." - Wooderson
'14 carbon Synapse - '12 CAAD 10 5 - '99 Gary Fisher Big Sur