friends setting together drinking coffee Twenty Something East Portland

An iconic city that represents everything the Pacific Northwest stands for, Portland is a haven for bicycle-riding, coffee-slurping craft beer addicts, who shop at farmers markets and vintage clothing stores.

But all hipster stereotypes aside, the West Coast city has many different personalities and flavors to offer its visitors; from posh waterfronts and brick-lined downtown streets to quiet quaint Nob Hill, there is much more variety to Portland than it seems at first glance – but if you are looking to experience the heart of Portland's spirit, head to the Eastside.

Consolidated into Portland city proper in 1891, the neighborhoods that lie east of the Willamette River used to be its own municipality named – you guessed it – East Portland. Today, this side of the river is the epicenter of underground culture, and includes Belmont, Hawthorne, Division/Clinton, Central Eastside, and the Lloyd District.

A rapidly-growing hub for food, drink, nightlife, fashion, arts and culture, there is an overwhelming amount of hip sights, smells and sounds to take in; but follow our tried-and-tested guide to East Portland, and you won't have to be overwhelmed.

Settling Down

Jupiter Hotel: What used to be a 60's motor lodge is now Jupiter Hotel, a charming Mic Century-themed accommodation with lots of artsy vibes and zero pretentiousness. Located in the convenient heart of Central Eastside, each room includes a hand painted wall, chalkboard doors, and easy access to an al fresco dining area downstairs and the Doug Fir bar next door. The staff are also top-notch and a great resource for navigating the lay of the land.

Gettin' Around

The taxi scene in Portland is pretty laughable (you can never find one anywhere, and they take forever to show up), but thankfully Uber came along to save the day. More power to you if you insist on a cab – but it'll cost you about $40 versus $25 for an Uber. The East end of Portland is especially walkable, or do as the locals do and take the streets by bike (fixie, of course).

Coffee Break

Tōv: Coffee is serious business in the Northwest, and there is no shortage of fine craft roasts in Portland. Tōv, however, is the only spot to grab a traditional Egyptian coffee, and on a double-decker bus to boot. The tented sunny rooftop deck and bold spiced flavors will whisk you away to faraway lands. If you're craving something earthy, authentic and highly-caffeinated, the Turkish coffee is your best bet, while those looking for something subtle and slightly sweet will have to go for the Nectar of the Gods latte – no debate.

Shop 'til You Drop

Vintage Pink: If you love vintage, you will seriously adore the hidden treasures in the Southeast 'hood. While there are plenty of stores along this stretch of Hawthorne you can go crazy in, Vintage Pink is a crowd-pleaser for its admirable selection of sweet secondhand furniture, home decor, and clothing. No matter how many drinks you had the night before, you can’t miss it: the building is bubble gum pink...with polka dots.  

Jackpot Records: What's a Portland trip without exploring a local vinyl store? With a vast collection of every genre from every era under their roof, Jackpot Records is friendly and diverse, satisfying every taste.

Brunch 'n Lunch

Jam on Hawthorne: When you see the line of hungry hipsters, couples, and families downing coffee from the self-serve cart on the sidewalk, you know you’ve come to the right spot. Jam has a little something for everyone, from the hardcore vegans to the pork lovers. The JD Massacre is a life-changing vegetarian sausage wrap after a long night.

Cartlandia: Portland’s seemingly adorable food carts shouldn't fool you into thinking they're not serious business. They’re magnificent, especially when they unite in a parking lot to create a place-like Cartopia, found on the intersection fo Adler Street and 9th. Chicken and Guns is a must, as is adding an egg on anything you order. Make sure to leave room for poutine at Potato Champion.

Chill

Serra: You didn’t come all this way for the legal marijuana, right? Didn’t think so. But just in case you want to see what the whole weed retail experience is like, pop into one of the many dispensaries gracing nearly every block in the city, like the beautiful and tastefully-designed Serra on Belmont. The helpful staff will gladly school you on the greens menu, and there are oodles of high-end accessories you can admire while sipping on a complimentary cup of Jasmine tea. Pure class.

Munchies

Blue Star Donuts: There’s an ongoing debate in Portland about who has the best doughnuts. While Voodoo is certainly popular with its outlandish cereal-topped options, sweet-toothed locals know Blue Star is where it’s at. The Blueberry Basil Bourbon is a classic, and so is the Hard Apple Cider Fritter. You really can’t go wrong here; try the alcohol-injected options if you're looking for some yummy novelties.

Salt + Straw: Just down the street from famous Pok Pok Thai, Salt + Straw is an icon in its own right. The craft ice creamery is so famous that it has its own Los Angeles outpost, although the PDX original is still obviously the best. Inventive flavors such as pear & blue cheese, green apple & wasabi flowers, and wildflower honey with ricotta walnut lace cookies will show you why there are lineups outside their door every day.

Play

Bagdad Theater: Portlanders either love or loathe McMenamins, because they’re a local chain. But the truth is, they preserve some pretty kick-ass historical buildings by turning them into adult-friendly entertainment venues. Bagdad Theater is an iconic movie theater on Hawthorne that serves pizza and handcrafted ales, courtesy of McMenamins. No matter your hipster stance on chains, you can’t argue with that.

Sassy’s: So, yeah...strip clubs are kind of a big deal in Portland – there’s something for everybody, including the world’s first vegan strip club. Sassy’s is a beloved landmark in Portland, and many claim it’s the best. Boasting 30 beers on tap and a daily happy hour, if you want to take home some pole-dancing moves as a unique souvenir, this is the place to be.

Dinner Date

Pok Pok Thai: Specializing in the North and Northeast regional cuisine of Thailand, Pok Pok has exploded into multiple locations thanks to its literally finger-licking good fare. Best enjoyed with a group of friends, share the famous chicken wings and some imported beer underneath the twinkling string lights.

Dranks

A local legend since 2012, Base Camp Brewing has been crafting their innovative brews in their spacious taproom on the East side for a while – so they know what they're doing. Their s'mores stout was basically made for Instagram, while the food trucks parked in their backyard make for convenient food pairings.

Night life

Holocene: Not so much a clubbing city than a grunge, indie and underground house kind of city, Portland's Holocene used to be an auto warehouse and is one of the best places to get down 'n' dirty. They also hold regular comedy nights and great 90s dance parties, so get those dance moves ready.