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Frisky City Guide: 10 Things To Do In Portland, Oregon

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Judging from the excitement surrounding the third season of “Portlandia” and all the emails in my inbox from readers who want to know more about visiting the city, Portland is having another moment (our really big moment happened back in the early 00s when The New York Times realized that not only did Portland exist, but the people here have beards and eat artisanal cheeses–it’s like a trend piece wet dream!).

When I asked my Portland friends for recommendations of things to do in this weird, wonderful city, their suggestions ranged from “Streak across the Steel Bridge” to “Drop out of graphic design school” to “Occupy something,” so obviously the Portland experience is tough to encompass in a single list (or even a single trip), but I’m going to try to focus on 10 activities that will guarantee a fun, fulfilling trip. Oh, and maybe finally convince my NYC-based Frisky coworkers to come visit me…

1. Take a hike. One of the coolest things about Portland (and one of the reasons so many Portlanders feel that it is acceptable to wear performance fleece jackets out to dinner) is that you don’t have to leave the city to go on some amazing hikes. I don’t even like hiking that much, but man, it’s hard to pass up some of the gorgeous trails here. One of the entrances to Forest Park–a 5,000 acre urban oasis with 71 miles of hiking trails–is just a few blocks away from NW 23rd Ave, a bustling shopping street. Mt. Tabor is a bit more out of the way in southeast Portland, but it’s still well within city limits, and after a brisk walk up to the reservoir, you can plop down on the grass and watch the sunset over the city (grab some bread, cheese, and beer from Cheese Bar down the street if you’re in the mood for a simple, delicious picnic). Remember in “American Beauty” when Ricky Fitts is like, “Sometimes there’s so much beauty in the world, I just can’t take it”? Be warned: if you take a sunset hike at Mt. Tabor, you will probably have one of those moments.

2. Drink some beer. After all that hiking, you deserve a drink! Luckily for you, Portland boasts a staggering amount of bars serving up mouthwatering local brews. Try the Lucky Lab, Laurelwood Public House, Beer, Gotham TavernMigration, Cascade Brewing Barrel House, or Horse Brass. If you like your alcohol with a side of irony and 90s arcade games, go to Ground Kontrol. If you want to drink in a beautifully renovated historic building, pop into one of the McMenamins pubs sprinkled around the city (the food is pretty mediocre, but the gorgeous atmosphere more than makes up for it).

3. Grab some coffee. Life in Portland involves a careful balance of beer and coffee drinking in order to maintain a constant buzz. When it’s time for coffee (and it’s always time for coffee), head to any Stumptown for excellent espresso. The Dragonfly Coffee House is a super cute and cozy option in Northwest, perfect for resting your legs after lots of walking. Caffe Umbria is a fabulous Italian coffee house in the Pearl District. If you’re on the east side, do yourself a favor and get a honey vanilla latte and croissant from Crema.

4. Stop and smell the roses. As I mentioned in my floral travel roundup, the International Rose Test Garden is seriously one of the most beautiful places in the world. Perched high up in Washington Park, with an amazing view of the Portland skyline, the Rose Garden is home to more than 7,000 roses of 550 different varieties. Take a stroll through this colorful wonderland in the spring or summer, and be sure to bring your camera, because the Facebook profile picture opportunities are endless.

5. Get lost at the book store. I don’t mean “get lost” in a metaphorical way, like “Get lost in the magical world of literature,” I mean you should go to Powell’s, the largest independent bookstore in the world, and literally get lost. You haven’t really experienced Portland until you’ve wandered through the maze of shelves in the rare book room, sipping a cup of coffee, inhaling the smell of old books and realizing you don’t have the slightest idea how to find the exit. Not that you’ll ever want to leave, but still. It’s kind of a rush.

6. Find the perfect vintage dress. Vintage shopping in Portland is great because it’s friendly, affordable, and, for a city that’s not exactly known as a high fashion metropolis, shockingly stylish. There are tons of vintage stores to check out, but a few of my favorites are The Red Light (huuuuge selection), Wanderlust (cutest store ever–I can’t leave without buying something), and Magpie (my go-to for funky costume jewelry).

7. Care about soccer. Portland city leaders tried really hard to get us a baseball team, but everybody crinkled their noses and said, “Baseball? Really?” Obviously the national pastime was waaaayyy too mainstream, so we got a professional soccer team instead, the Portland Timbers, and now everyone is obsessed. Every game includes a chainsaw-wielding mascot, and a huge group of super fans called the Timbers Army always keeps the energy up. Basically, if you get the chance to attend a Portland Timbers game, you probably want to take it–and don’t worry, the stadium serves local microbrews.

8. Buy something handmade. Whether you’re interested in buying beautiful handmade crafts or watching white dudes with dreadlocks play bongos, plan to spend an hour or two at the Portland Saturday Market, a massive outdoor market that runs from March to December.

9. Eat breakfast. It’s a well documented fact that Portlanders go hogwild for brunch. It’s our favorite meal of the day, and there are tons of great spots to satisfy your craving for waffles, biscuits and gravy, eggs benedict, or dangerously large piles of meat. Check out Tasty n SonsKenny and Zuke’s, Podnah’s Pit (I saw Carrie Brownstein here once, so I assume it’s “Portlandia”-approved), Broder, Isabel, Mother’s, or Pine State Biscuits.

10. Then eat some more. I’ve actually been staring at this last one for like 5 minutes, because the Portland food scene is so expansive and delicious that I have no idea how to sum it up. Let’s just go rapid-fire, shall we? The double burger at Lardo. Solstice stew at Caldera. Pizza at Apizza Scholls. Vegan breakfast bowls at Canteen. Nutella banana waffles at The Waffle Window. Pad See Ew at Mai Thai. Dill pickle soup (yes, really) at Otto and Anita’s. Pulled pork sandwiches at Bunk. Shrimp dumplings at Shandong. Tacos at Por Que No. Handmade ice cream at Salt & Straw. Butterscotch budino at Nostrana. There are so many amazing restaurants (and food carts!) in this town that I could go on forever, but the gist of it is: if you’re visiting Portland and aren’t constantly chewing, you’re doing it wrong.

If you live in Portland or have been here in the past and have other ideas to add to the list, please share them in the comments! And if you’ve never been, well, I hope to see you soon!

Email the author of this post at winona@thefrisky.com. Follow me on Twitter.

[Photo by Shana Lee]

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