One person asked
Name three places in Portland (besides Powell's City of Books) that you would take a first-time out-of-town visitor to see.I've actually been wondering this, and I don't want to be either obvious or intentionally weird-for-weird's sake. I could take people to the recreated-after-several-years 24-Hour Church of Elvis, but worry about my motivation for doing so. Also I miss when it was an actual shop space people could go into. Also also I miss that I never did that. Also, also, also, I know enough about the curator of the 24-Hour Church of Elvis and the difficulties she's been through that if I met her again -- I actually have met her briefly, once -- I'd want to hug her. And that might be awkward for both her and my guests.
Portland does what it can to be a very functional town. We seem to want landmarks that can be used on a commute. We'd never have something like the Space Needle because A) we haven't had that big an expo in town since the 1905-06 Lewis & Clark Exposition (go here and scroll down for more images) and I think we're unlikely to do so again soon, and B) you can't live or, with few exceptions, work in the Space Needle, can you? You go up, look around, maybe buy knickknacks and/or a meal then go down. So we have stuff like the Aerial Tram between Oregon Health Sciences University's two campuses, one on a hill and one on the water. We also have the Eastbank Esplanade, squeezed between a freeway and the Willamette River. Sometimes above the river, because that was the only place to put a path. These are routes. These are also a couple of places of really, really nice vantage points from which to look at the city.
I'd get visitors to the tram, for at least a round-trip, maybe two. That's one place to go. Because I've never been there and would like to go, I'd consider taking them to a built-up garden in NE Portland called The Grotto -- a botanical garden and Catholic shrine, with (among other things) a chapel built into a cliffside. That's two. (Or we could do the more standard Washington Park over in SW Portland, overlooking downtown. It has a bunch of test gardens, forests, memorials, our zoo, and even little trains that run through the zoo.
I'd also get them to one of Portland's two Voodoo Doughnuts. C'mon, gotta be obvious about that! The original downtown one is tiny and with a wait, but is open 24 hours; a never, larger, and still funky one on NE Sandy is open almost 24 hours, though not quite. (Portland's more likely to have stuff almost open 24 hours a day than stuff actually open 24 hours a day.)
Going outside the city yields even more possibilities: mountains, the Coast, waterfalls, and the Maryhill Museum of Art, a place I became deeply fond of while living in Eastern Oregon. I go there, I just feel calmer and happier. It's a mansion and museum in the middle of what looks like nowhere, overlooking semi-desert and also hosting many, many original Rodins. It's improbable and, in its way, beautiful.
Stuff just peels off of Portland, so I could go "We should see this! And we should see this! And we should go further and see that!" Or I could have future visitors read Chuck Palahniuk's Fugitives and Refugees: a Walk in Portland, Oregon, which is somewhat out of date but far more thorough than this post can be.
And if certain people I'm friends with visited, I'd finagle a reason to go to NE M.L.K. Blvd. and drive past Harder Mechanical Contractors, so they could see the word "HARDER" in giant letters on the side of a building. ;-)
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Also! Someone else asked
If money were no worry, where would you like to be in 5 years?Still in this town, unless I've met someone REALLY COMPELLING who lives elsewhere and wants to hook up with me. And honestly, if that happened, I'd probably try to get Ms. Whomever to get over this way and try this area for herself. (You can tell I like this region.)