Portland is weird. So are you. It’s a perfect combo.
Here's how to plan the ultimate vacation in a city that demands you leave weirder than when you came.
Portland is situated on the edge of the rushing Columbia River, adorning Oregon like a crown. It is a city whose spirit urges you to be your strangest and most authentic self!
Though the City of Roses is small, its vast hodgepodge of eccentricities makes it seem quite large. Portland has a gently electric personality—a swagger that walks with you as you stroll down rain-slicked streets, deciding how best to spend your day. You could explore and have an adventure in one of the many gorgeous parks or perhaps take in the vibrant works and personalities of the Alberta Arts District.
Portland welcomes all and has so many gems in her crown that it’s nearly impossible to choose what to do first! Let’s help you plan the ultimate vacation in a city that demands you leave weirder than when you came.
THE PEARL DISTRICT
If you’re looking for lively, craving style with a sprinkle of sweetness, and most importantly, if you are geared up and ready to hit the town, start in the Pearl District. It is a distinctly hip and vivacious neighborhood nestled on the western side of the Willamette River, offering a sense of character and charm that sweeps you away. Picturesque streets adorned with twinkling lights and bright storefronts make the perfect backdrop for your impromptu photoshoot or spur-of-the-moment coffee date.
POWELL’S CITY OF BOOKS
First up on our adventurous tour of this strange city is the world-renowned bookstore, Powell’s Books. If you are a bibliophile, we beg you to treat yourself by spending some time here. When we say “spend some time,” we mean it. This iconic bookstore is the largest new and used bookstore in the world! Sprawled across an entire city block and housing ten separately themed rooms, including a rare books room, you could easily spend an entire day browsing their magnificent collection!
With over a million titles, an inviting coffee shop, and a bright and organized aesthetic, this “city of books” is a piece of Portland you won’t want to miss!
FIRST THURSDAYS
Who doesn’t love a good art festival? First Thursdays in the Pearl district are always delightful, with incredible local art, food, music, and plenty of artisanal goodies! For over 30 years, streets have shut down, and galleries have opened to offer people a chance to wander and delight in the city’s artistic gifts.
If you are looking for a one-stop shop for a “get to know you Portland” event, this is the place to be! Not only will you get the opportunity to view stunning works, but you will also have the chance to talk to this fantastic city’s local artists and creatives! Parking can get nuts, as it is always packed with people, so plan ahead!
CULT
If you’re looking for something to immortalize your trip to the weirdest city in America, you will leave with a whole suitcase full of goodies after stopping here! The moment you step through the doors, you will be welcomed by the sight of dozens of strange, wonderful, and unique gifts. From quirky collectibles to distinctive local art, CULT is known for its carefully and creatively curated floor of goodies.
NORTHWEST
As you wander the streets of the Northwest district, take in the long streets strewn with gorgeous historic buildings and endless shops. Considered one of the best neighborhoods for shopping, this area is bursting with vibrancy and the unique energy that Portland is famous for.
Hop on the streetcar and spend a day wandering this upscale borough, taking in the vintage boutiques, gourmet restaurants, and stylish bistros.
ELEPHANT’S DELICATESSEN
This is one of the cutest places where you will ever order a sandwich and buy a jar of tapenade. For 43 years, this from-scratch deli served the community. If you’re meeting a date for lunch and want to take them somewhere whimsical, you can’t go wrong! The open-air kitchen lets you watch your pizza baking in the classic wood-fired oven or the chefs craft a scrumptious sandwich.
The decor is a cottage-core lovers’ dream. After your meal, wander the dark oak and tiled floor and take in the packed space full of baskets and shelves stuffed with homemade sauces, salads, and European-style snacks!
BUCKMAN/HAWTHORNE
Across the river from downtown Portland sits one of the most popular neighborhoods for superior dining and distinctive microbreweries. There are so many individual and local delights dappling the streets that you might as well get a hotel room on this side of the river to experience as much as possible.
SISSY BAR PORTLAND
While sipping on a carefully crafted cocktail and enjoying the best Columbian food in Oregon, you will feel instantly cared for at this LGBTQ+ haven. This sleek and moody bar offers a lovely patio to soak up the sun on days when the perpetual Pacific NW rain ebbs.
There is no need to check the website to see if something fun is happening; there is a constant slew of exciting dance parties, broadway sing-along nights, and happy hour drag shows! Celebrated for its exquisite meals and superior service, Sissy Bar stands out in a neighborhood known for nightlife.
BAGDAD THEATER & PUB
If you’ve spent time in Oregon, you know the name McMenamins. The Bagdad Theater & Pub is unique as it doubles as a European-style cafe/bar with delicately tiled floors and gorgeous floor-to-ceiling doors that create an indoor/outdoor patio feel.
What is truly magnificent about this venue is the nearly hundred-year-old movie palace connected to the bar. Truly staggering art deco style adorns every inch of this unaltered 1920s jewel. There’s no need to grab dinner beforehand; you can order a delicious basket of fish and chips and eat in the theater!
ALBERTA ARTS DISTRICT
If an entire neighborhood could feel like a giant farmer’s market, this piece of paradise nails it. Cradled in NE Portland, this vivacious area has paintings, murals, and street art on every block. During the summer, on the last Thursday of every month, the streets close down to traffic and bloom with vendors. Meander the pavement, taking in the endless galleries, breweries, and music venues!
URDANETA
Effortlessly blending the Spanish countryside’s rustic romanticism and Madrid‘s bustling energy, Urdaneta is about to become your favorite tapas bar. The distinct open-air kitchen and lively seating area will awaken your senses before the stunning plates reach your table.
The decor is casual, and the servers are friendly and knowledgeable, creating an environment of jovial relaxation. Drawing inspiration from the aromas and ambiance of Spain while using fresh, local ingredients native to the Pacific Northwest, Urdaneta is a truly unique experience.
ALBERTA STREET PUB
Are you looking for a place to order pancakes made with Bailey’s Irish Cream and sing karaoke? Boy, have we got the spot for you!
For over 30 years, this watering hole has provided a sense of community to the Alberta Arts District. Its mission is to create a welcoming space for artists and musicians to express themselves and for the locals to enjoy the magic of Portland. From songwriting symposiums and trivia nights to queer dance parties, there is always an exciting event to get you out of the rain.
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