The best thing about living in Portland is the quirky culture. People are friendly and helpful and appreciate good design and great food. Plus, it's a well-kept secret that the summers here are fantastic, and the rainy winters really aren't that bad.
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My favorite shops in Portland are Flutter (gifts and accessories), Pistil Nursery (indoor and outdoor plants), Paxton's Gate (beautiful natural curiosities), Powells Books (not just the main location downtown--the ones on Hawthorne are great, too), Schoolhouse Electric (beautiful home goods), Cargo (imported treasures), Shop Adorn (clothing and accessories) Alder and Co (housewares and gifts), House of Vintage (tons of clothing, furniture, and knick-knacks), The Red Light (vintage clothes), Radish Underground (women's clothes from local designers), Francis May (high-end clothes), Backtalk (women's new and vintage), Sloan (women's clothing), Grand Marketplace (huge space full of vintage furniture and accessories), Animal Traffic (vintage clothes).
SCRAP (http://scrappdx.org/) is the first place I look for many craft supplies. They're a non-profit creative re-use store. For miscellaneous supplies (paint, paper, jewelry, stamps, washi tape), I go to Collage. For general art supplies, Columbia Drafting Supply or Muse are good. For fabric, try Mill End Fabrics, Modern Domestic, Bolt, or Fabric Depot. I really like Dava Bead for beads and jewelry-making items.
The Crafty Wonderland shop and the Portland Flea are the first places that come to mind for crafters to sell their crafts, though tons of local shops (and even some national chains) sell locally-made items alongside their other offerings. Portland has a long tradition of supporting local makers with the Portland Saturday Market (both days of the weekend, despite the name), though it skews to the older generation. There are also seasonal fairs (like Crafty Wonderland) that spring up for holiday gifts, and during the summer the streets are crowded with vendors hawking handmade items at Last Thursday on Alberta.
For inspiration I recommend going to The Portland Art Museum which is fairly small, but has interesting events and art. Oregon Museum of Science and Industry (OMSI) is fun, especially if you like science or have kids. For some gorgeous architecture, drive through the West Hills and look at the houses perched precariously on the hillside. Long city walks through cute neighborhoods (the Laurelhurst, Overlook, and Ladd's Addition) are a fun way to discover new inspiration. The downtown Multnomah County library is lovely, and has inspired at least one song (by the Decemberists).
Taking a stroll downtown, or down one of the big retail streets (Hawthorne, NW 23rd, Mississippi, or Alberta) is always great for shopping and people-watching. And if you leave Portland without visiting Powells Books, you've made a terrible mistake.
There are some fantastic parks within city limits. Some of my favorites are Cathedral Park, Peninsula Park, Forest Park, Mt. Tabor Park, and Laurelhurst Park. The Japanese Garden, Rose Garden, and the Chinese Garden are all super photogenic and wonderful to visit. You can also drive to the Oregon coast in less than two hours and see tidepools or foggy vistas, or visit the Columbia River Gorge and look at the many spectacular waterfalls. Multnomah Falls is a must-visit if you've never been, but Oneonta Gorge and Beacon Rock are a couple of spots I've visited recently that are great.
The bridges (any of 'em!) are pretty photogenic, but the most iconic Portland things to take photos of are probably the Made in Oregon sign and views of Mt. Hood. It's only visible on clear days, and on extra-clear days, you can see Mt. St. Helens.
Eat & Drink
This is a tough one, because there's a ton of amazing food in this town. From food carts to fancy restaurants, it's hard to go wrong. Here's a variety of places I'd happily eat any day of the week:
Natural Selection, Screen Door, Brass Tacks, Por Que No, Irving St. Kitchen, Produce Row Cafe, Montage, Prasad, Sizzle Pie, Biwa, Ava Gene's, Lovely's Fifty Fifty, PBJs Grilled
Brunch: Jam on Hawthorne, Gravy, Miss Delta, and a bunch of the above places (especially Screen Door, but the wait is epic) also do amazing brunches.
If you're looking for coffee or a sweet treat, Salt & Straw, Blue Star Donuts, Ruby Jewel, and Pix are all delicious.
Top bars to hang out in include The Bye and Bye, Victory Bar, Doug Fir, Radio Room, Rontoms, Dig-A-Pony, White Owl Social Club, Kennedy School, and Ground Control are all good places to start.
I'm not really sure--I do most of my crafting at home. But this town is so DIY-friendly that crafting would be welcome at most any park or cafe, and it would probably be a great conversation-starter.
The only one I'm aware of is the Rose City Yarn Crawl (http://www.rosecityyarncrawl.com/), which has a pretty epic reputation.
Practically anywhere! You can't throw your knitting needles without hitting somebody crafty around here. Taking classes in a medium you'd like to learn would be a great way to meet other crafters, though. Many of the fabric stores around town have sewing classes, Collage has classes in a lot of different techniques, and Dava Bead and Trade has metalworking classes that I've taken.
See Something Special
Portland has its own incredibly popular urban goat herd. They even have their own blog (http://thebelmontgoats.org/), and they keep multiplying, having adorable little kids two at a time. Visiting them is really fun, since most of them are pretty friendly, and if a caretaker is around, you can even go into their pen. They currently live on an empty lot in SE Portland, but sometime soon they'll be moving to a new location that will still be publicly accessible.
There's this weekly tradition here called "Zoobombing," where people ride tiny bikes down a steep hill near the zoo and into the city, screaming on the way down. Between rides, their tiny bikes are kept locked up on a tower downtown as an art piece. There are a lot of more traditional sculpture pieces and fountains around town that are fun, too.
There's a cool retro-futuristic aerial tram that you can ride from the waterfront to the top of the hill where Oregon Health and Sciences University is located, though I still haven't ridden it!
If you're a fan of the show The Simpsons, you can keep your eyes peeled for streets that Matt Groening named characters after--just google "Simpsons map of Portland" for ideas.
Take Home A Souvenir
Voodoo donuts are a pretty popular souvenir, as are local beers or spirits. For a more long-lived memento, support the designers here and bring home some Portland-made art, clothing, housewares, or accessories.
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