THE pipe store in Portland is Rich's (
http://www.richscigar.com/)
both of my good pipes are from them, although I like some of the blends that Paul's Cigars has and you can smoke in their west side (Beaverton) store.
For a cigar, there is no place better than a Stumptown herf. Rumors abound (as far as I can tell ... I'm jet lagged) that a herf at the Shilo is planned. Give us real dates (I'm Catholic, but have no idea when Easter is) and we'll "git er done".