It's not hard to find things to do in Portland--far from it. What's hard to do is figure out what you'll really enjoy in Portland. Having lived here for a few years, I know what I like to do. So here's a list of the things we recommend to like-minded people.
At Mississippi's Bridge City Comics Taylor working the merch booth for Marian Call and the Doubleclicks.
There are Powells all over the city, but to truly appreciate the immensity of this thriving book store, you should stop by the original.
We have one must-do in Portland, and that's Ground Kontrol. This arcade has all sorts of video games and pinball machines for cheap--like $.50 a play. And it's a bar, so no kids after 4pm.
A great place to gather for board games is Guardian Games, as they have games for rent as well as access to alcohol in a relatively quiet space.
Other events vary throughout the month, but the best place to look for activities is at the Geek Portland website.
Portland has more breweries per capita than any city in the world, so it's pretty impossible to avoid them. We like to bring out-of-town guests to Henry's which sports 100+ beers on tap and allows you a good sample of what you might get other places. However, people who already have their favorites might want to try out the brewery directly.
Rogue - home of American Amber, Dead Guy, and the infamous Voodoo Maple Bacon beer in the pink bottle.
Deschutes - Black Butte, Mirror Pond and Obsidian Stout, among others.
Bridgeport - India Pale Ale, Cafe Negro, and Hop Czar, and more
Widmer - Hefeweizen, Drop Top, and Drifter.
The New Deal distillery spirits tasting
Not to be outdone by their lower alcohol-content brothers, the liquors in portland are developing quite a following as well. Conveniently, they're all located within walking distance of each other in a part of town called Distillery Row. You can get a passport to receive discounts on tastings at the distilleries, or you can just spend a few dollars at each.
These are the neighborhoods you are most likely to visit when coming to Portland. Each has its own personality and unique set of things to see. All are within 10 miles of each other, and relatively easily reachable by public transit. The Trimet website is especially useful for planning trips, and the iphone app is indispensable for up-to-the-minute bus and train information. If you plan on getting around the city without a car, I highly recommend these resources.
Pearl District: Located immediately outside of the train station, the Pearl District contains the bustling brewery blocks, Powell's, many boutiques and eateries, art galleries, and my favorite cupcake shop, Cupcake Jones. You can't help but visit the Pearl on your first time to Portland, and it's worth wandering around to discover what might appeal especially to you.
What a grilled peanut butter sandwich looks like right before you eat it. The green is jalepeno.
Alphabet District: As the most consistently upscale part of Portland, The Alphabet District is increasingly popular as a "magically hobo-free" alternative to the Pearl District. This isn't to say that all the stores and restaurants are out of the average traveler's price range, but many of the shops strive for an level of class over quirk uncommon in other districts. A great place to stop while walking is PBJ's Grilled peanut-butter and jelly cart that concocts sandwiches that must be tasted to be believed.
Hawthorne: Although the Wikipedia entry points calls the heart of Hawthorne as between 30th and 42nd, an industrious walker can take in the whole street in a half a day. Whether you begin at the Hawthorne Bridge or Mount Tabor Park, you'll have plenty of reasons to stop and eat, or shop, or linger for a people-watching session. Prepare a couple of dollars for the street musicians you'll more than likely pass. And make sure to stop for a treat from Jaciva's, the bakery with the best cakes and cookies in Portland.
Mississippi: Unlike the Pearl and Hawthorne, you can take in the interesting parts of Mississippi in a few hours. The distance of the entire street -- from Fremont Street in the south to Skidmore on the north -- is only half a mile but is packed with unique stores, eateries, breweries, and a food cart pod. For a treat, I recommend Ruby Jewel Scoops--a "small batch artisan ice cream" shop that will knock your socks off.
The Great Outdoors:
Washington Park: Home of the Portland Zoo, The International Rose Test garden, the Arboretum, and the Japanese Gardens, (and more) Washington Park contains a day's worth of activities. Although much of the park is free, plan on spending about $10 for entrance to each of the museums as well as the Japanese Gardens. And don't forget to venture outside of the park center to see a selection of Portland's mansions. Or walk toward the Southwest corner of Vista and Burnside to SW Green Avenue for a few hundred yards of street straight out of europe. If you take this option, feel free to walk a few blocks north on Vista/NW 23rd to Sunny Day Coffee for a strong brew, a fresh treat, and some friendly conversation.
Forest Park: A huge park 8 miles from one end to the other, Forest Park is a great way to go for a hike in the middle of the city. You can grab a set of maps for the trails or just explore on your own, and you know you're never more than a mile away from civilization.
The Chinese Garden: Although smaller than the Japanese Garden in Washington Park, the Chinese Garden has the advantage of being in the dead center of the downtown area. More statues and ponds than trees and waterfalls, the Chinese Garden also hosts a tea shop with "tea presentations... in classical styles with snacks and sweets offered as compliments" -- a delightful way to refresh yourself in a busy day of sightseeing.
The touristy stuff:
24 Hour Church of Elvis: An art installation that honors all things campy about roadside attractions, aka tourist traps, the Church of Elvis is worth seeing for a few minutes, if only to feel a bit ridiculous.
Voodoo Donuts: Voodoo donuts is home to, among other things, the maple bacon bar, which has become so well known as to be cliche. If you visit Portland and don't do Voodoo, everyone at home will be very disappointed in you, but know this: Voodoo donuts aren't great donuts, they're just quirky.
Saturday Market: A flea market that's turned semi-permanent, Saturday Market hosts a variety of (usually) independent vendors selling their wares. The glut of tourists (and locals showing around tourists) also brings in a variety of performance art and fantastic food. It's only open on Saturdays and Sundays, and only for part of the year, but it's a great way to see a cross section of Portland all jammed into one place.
Portlandia locations: People are always asking if the show Portlandia is true to life in Portland. The simple answer is, of course it is. In fact, when we started watching the show we were sure it would fail because so much of the humor seemed like inside jokes.
This is in no way a comprehensive set of Portland locations, nor does it cover parts of the city that don't interest me (like its robust exotic dancing scene. I recommend looking into Chuck Palunuck's Fugitives and Refugees: A Walk in Portland, Oregon for much more information on that.)
Well, Portland friends, did I miss anything?