I can only handle the Portland stuff... Pittock Mansion Pioneer Courthouse Waterfront Park (right on the Willamette River) NW 23rd Ave. area (shopping/dining area, a little comparable to State Street in Madison) Kornblatt's Deli (on NW 23d, I miss this place a LOT... we lived nearby & ate breakfast there many weekends) Pearl District (upscale part of downtown, pricier shops & restaurants but nowhere near prohibitively expensive) Powell's Bookstore (if you go, do not miss the rare book room) Voodoo Doughnut (don't miss this! can have long lines; I've only been to the SW/original location) International Rose Test Garden Japanese Garden Mt. Hood I could probably make a list just as long with excellent microbreweries, if you're into good beer. I'd be happy to compile that list separately for you from this post, if desired. I think I posted in the Beer Thread about that very thing once upon a time, so hopefully that post wouldn't be hard to find. The food in general in Portland is fantastic, I won't even try to start a list for restaurants. - Also, Matt Groening is from Portland. Many characters on the show are named for things in Portland, especially the streets in the Alphabet District. Burnside St. is the main E-W artery in Portland, and in the NW section of the city, the streets ascend block-by-block to the north in alphabetical order. Burnside, Couch, Davis, etc. Notable names in that section would be Lovejoy, Flanders, Kearney, Quimby ("Burns"ide too). The shopping/dining district I mentioned on NW 21st Ave. is right in this neighborhood, so you don't need to make any special trip just to see street signs - Two semi-mildly-important pronunciation tips: it's the Will-AM-ette River, & Ore-gun... the locals tease you that "it didn't go anywhere" if you pronounce it Ore-gone - And to clarify the NW/SW designations, the town is referred to in terms of NW/SW & NE/SE areas. It'll make sense once you're there. - If you have a rental car, a tour of the nearby wine country is always fun. Free samples! Alright, I think my brain is tapped for now. I'll add anything else if/when I think of it. Portland really is a great city. The light rail & streetcar lines make the city (especially NW area) incredibly easy to explore. Be sure to take advantage of that, since like any city, parking can be an issue.