The umbrella will make you look like a tourist. Get some Tevas and a fleece jacket.
Where are you from? If you are from an area that gets Deschutes anyway, focus on getting HoTD and Cascade stuff while you are in town as the distribution on those is poor. While I avoided it nearly completely when I lived in PDX (pre smoking ban), The Horse Brass is now one of my favorite beer bars. Belmont Station (no longer conveniently next to The Horse Brass or on Belmont) is a great bottle shop and serves a few interesting draught beers in their cafe.
Widmer usually has interesting stuff at the pub and better German food than the German restaurants in town.
If you like Thai food go to Pok Pok. Thank me later.