Guide to Solo Travel in Portland, Oregon

Updated: Dec 19, 2020

You know it’s going to be a great trip when the first night begins with tequila shots and ends with several donuts. Aside from the increased risk of coronary heart disease, I fell in love with Portland. As Julie Andrews would say, “The city is alive with the sound of the 90’s,” or something like that… This city truly amazed me. If I hadn’t grown up in California where “bad weather” refers to the two times a year that it drizzles, I would absolutely move here. So pull your computer screen close, kids. It’s time for a new edition of “Traveling Solo in the Pacific Northwest with Kathryn.”*


*(Editor’s note: Taking any of the advice in the above paragraph is probably detrimental to your health. Woof…)


The Pacific Northwest is home to some great cities, but there is something so unique about Portland. The unnerving kindness of strangers, the bright fall colors across the rainy skylines, and the Columbia River flowing proudly through the heart of the city are just a few things that made this destination one for the books.


To be honest with you, I felt totally in my element in this city. Why, exactly? Maybe it’s my uncanny way of relating with hipsters for unknown reasons. Maybe it’s my strong love of leather-bound books. Who knows. But man, something about this city made me walk down the streets with the kind of swagger you get from hearing the opening lyrics of The Beegee’s "Stayin’ Alive".


Before you can get to the swagger walk stage, you have to get to Portland. Thankfully, getting into town from Portland’s airport is a breeze. Uber is readily available, and there are set fares to most destinations downtown. My ride cost around $24. Easy, Breezy, Beautiful.


Where to Stay

Next, let's talk about where to stay. My trip to Portland signified my first solo trip, meaning I arguably am no expert on which neighborhood or providence to stay.


Although the resources are plenty, I would like to take a minute, nay, a fortnight, to bask in the glory of the Benson Hotel. I discovered this hotel on Expedia, but not before checking Airbnb and comparing prices. There was not much of a price difference between the two. And you know how much I use Airbnb, so consider this a rare and useful tip. WOW, Toot-Your-Own-Horn Tuesday much?

Another reason to stay at the Benson Hotel? Location, location, location. SO CENTRAL. I walked everywhere, so it was never necessary to take a cab.


The historic Benson Hotel has the glamour of old San Francisco with a twist of urban flair. The views, amenities, and charms surely will not disappoint. I was greeted with a beautiful charcuterie plate and a warm note from the staff wishing me a happy trip. I strongly considered staying in the spacious room, putting on the black bathrobe, and toasting "To Industry!" like a 1920's oil tycoon. However, I opted to explore the nightlife Portland had to offer instead. Compromises, you know...


The Pearl District

...Annnnddddd this pretty much sums up the night: zero photos, just a view of the sunrise from my hotel room. It consisted of multiple beers, late-night munchies, tequila shots, and Australian rugby games. If you are looking for a fun bar to visit, 10 Barrel in the Pearl District would be my top choice. There is an open-air patio on the second story that boasts lights, local brews, and a fun, young crowd. Get the Apocalypse IPA. It may lead to meeting some friendly strangers who take you to my next Pearl District favorite, Brix Tavern. LATE NIGHT HAPPY HOUR IS A THING, GUYS—delicious morsels of mac 'n' cheese, quinoa salad, and chicken tacos for half-price beginning at 9:30 pm.

Late-night happy hour is such a huge deal, and I cannot begin to put it into words. If you like spicy drinks, try the Zesty Mango -- it packs a punch. Jalapeno vodka should taste bad; it really should..but it does not. After munching on some delicious food, my new friends and I headed to the River Pig Saloon. The name alone should indicate that this is a place where you drink heavily and watch sporting events. You'll love the atmosphere and wrap-around wooden bar. To be candid with you, after that, I walked back to my hotel, ate some Pringles and M&M's from the minibar, and passed the hell out.


Voodoo Doughnuts