Is Portland, Oregon, the quirkiest big city in America? Quite possibly, yes. This famed hipster mecca is home to a 31-foot tall Paul Bunyan statue, recreational marijuana, and a kilt-wearing Darth Vader on a unicycle who plays flame-shooting bagpipes (yes, seriously), among other oddities.
As a city that introduces itself with the unofficial motto “Keep Portland Weird,” you already know you’re in for a good time no matter where you go, though we have a few personal recommendations.
With that said, here’s exactly where to eat, stay, and get super weird in the City of Roses.
Eat: Voodoo Doughnut
No trip to Portland is complete without paying a little visit to the deliciously eccentric Voodoo Doughnut, where the doughy creations range from the Bacon Maple Bar, Maple Blazer Blunt (it’s actually shaped like a blunt), the Old Dirty Bastard, and the Cock-N-Balls.
Arden
Small yet sophisticated, Arden is one of downtown Portland’s most intimate and impressive spots if you’re looking for a fantastic dinner with perfect wine pairings that are curated by owner and super-sommelier Kelsey Glasser.
The menu is small but perfectly executed with elevated dishes like wild king salmon and adobo lamb loin with almond salsa. If you’re unsure of what to order, get the Chef’s Prix Fixe with four delicious courses — but don’t forget the coursed wine pairing.
Saburo’s Sushi House
Sure, you’ve had sushi before…but you’ve never had sushi like this. Once you get past the line that often wraps around the building, this no-frills Japanese spot serves up mega sushi rolls and nigiri that are so big you have to unhinge your jaw to eat them. But not only are the rolls supersized, they’re super good, too.
Jackrabbit
Located in the Duniway Hotel in downtown Portland, Jackrabbit offers some of the best meat-centric bites around.
The French Onion Deviled Eggs puts an upscale and absolutely delicious twist on the classic hors d’oeuvre, and you can even take a trip “Around the World in 8 Hams” with an epic charcuterie board of 8 different hams from different corners of the globe.
Plus, they make a steak so good, you know that cow didn’t die in vain.
Mother’s Bistro
If you’re in the mood for some traditional comfort food like homemade pies, roasts, sliders, and dumplings that are all made from scratch, be sure to check out Mother’s Bistro.
Their portions (and cocktails and glasses of wine) are very generous, so you’ll definitely leave very full, very happy, and very satisfied.
Irving Street Kitchen
Right in the heart of Portland’s Pearl District (a.k.a. downtown), Irving Street Kitchen is home to the creamiest, richest butterscotch pudding in the Northwest, topped with a heavenly vanilla bean caramel and salt and peppercorn cookie.
Stay: Heathman Hotel
The historic Heathman Hotel in downtown Portland gained a certain popularity from being mentioned in the cheesy BDSM drama Fifty Shades of Gray (though no scenes were actually filmed there), but more importantly it’s one of Portland’s oldest hotels, having been around since 1927.
The tastefully appointed rooms are sophisticated and decked out in eclectic furnishings, and the hotel boasts an impressive art collection and thousands of books signed by the authors in the stunning library.
When hunger strikes, head over to the adjoining restaurant Headwaters for some fresh local oysters, or grab a drink from the bar to sip in the library.
Fun fact: The Heathman is often said to be one of the most haunted hotels in the U.S., so sweet dreams.
Sentinel
This posh hotel is nearly 100 years old and possesses one of the most dramatic entrances in Portland thanks to its grand Italian renaissance architecture.
The 100 luxe rooms and suites at the Sentinel feature emerald tones that represent the lush Oregon forests, and encapsulate the city’s unique style with Pendleton throws and oversized grey tweed headboards with brass nail trim.
The terrace suites offer sweeping views of the city, and the private outdoor fireplaces are a very nice touch for chilly Portland nights.
In the evenings, you can grab a drink at the Jackknife bar right off the lobby where the specialty is expertly crafted cocktails and beer.
Woodlark
Nothing screams “Portland” louder than a hotel that has local botanicals adorning the wallpaper, like at the herbal and very green Woodlark Hotel.
Dossier
This hotel is also located in downtown Portland and is perfect for those looking to explore the Pacific Northwest’s great outdoors thanks to its “Adventure Valet,” which offers guests complimentary backpacks filled with trekking poles, headlamps, waterproof phone cases, and dry bags.
Drink: Driftwood Room
Fancy a glass of absinthe? Head over to the Driftwood Room inside of the chic and retro Hotel DeLuxe.
Have a seat at the dimly lit and richly stocked bar, take your pick from an impressive absinthe selection, and summon the green fairy the right way with an absinthe fountain.
And in case you aren’t the biggest fan of absinthe, the Manhattan flight is also a good choice.
McMenamins Kennedy School
Hands down one of the most unique bars you’ll ever go to, McMenamins Kennedy School is a restored 1915 elementary school that’s been transformed into a venue consisting of four bars, a restaurant, and a hotel that’s equal parts spooky and awesome.
Flâneur Wines
Drive out 30 miles to the rolling hills of the Willamette Valley and you’ll find Flâneur Wines, where the grapes are grown organically 700 feet above sea level in true Oregon fashion. The winery also transformed a 100-year old grain elevator into a chic entertaining space for a truly unique experience.
Cannon Beach
Cannon Beach is small coastal city that’s a quick and very scenic 90-minute drive from Portland where you can go to kick it at the beach for the day. On even the hottest of days it’s breezy and comfortable, and the water is a nippy 60 degrees Fahrenheit.
But here’s an important word of advice: Portland and the coast is definitely better experienced with a car and finding parking is no problem at all, but the city is infamous for tricky one-way streets and odd intersections that are seriously hard to navigate.
So, if you’re renting a car (which we highly recommend) make sure to snag something with a good navigation system like an Audi A4 which has a virtual cockpit and navigation on the head-up display so you’ll never get lost or make a wrong turn.
Smoke: Electric Lettuce
If the name is any indication, Electric Lettuce is a recreational dispensary — and a groovy one at that. Super psychedelic decor with memorabilia from the 1960s and 70s makes (legally) buying weed a particularly fun experience.
“High, how are you?” is their motto, and their mission is to “bring flower to the people and celebrate the sordid history of marijuana use in America between 1965 and 1971” with “smoking accessories, cannabis edibles and topicals, concentrates and extracts, and grass, dope, reefer, or whatever they’re calling cannabis these days.”
Serra
This dispensary is named after the Italian word for greenhouse, which is fitting considering how green, bright, and terrarium-like it is inside.
Once you get over how fancy and relaxing the vibe is, you’ll find exactly what you’re looking for with Serra’s selection of flower, edibles, topicals, concentrates, and lifestyle accessories.