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

This leads me to wake up… As I approach my mid-20's, my body is throwing me a bone, if you will, with hangovers. I bounced back pretty quickly and woke up early, ready to seize the day, but not before doughnuts. If you have never turned on a television or live under a rock, Voodoo Doughnuts is pretty famous worldwide. Known for its kooky flavored treats, it is an absolute must-do when visiting Portland. Get there early!! I arrived around 9:00 am on Saturday and was in line for about 10 minutes, but the line gets longer throughout the day. They don't accept credit cards, but there is a convenient ATM inside the shop. Also, continuing on the theme of keen Portland locals, the gentlemen at the counter threw in a free doughnut just because. HE GETS ME, OK? You can see a few of the flavors I snagged above, including the maple bacon doughnut, which I will eat on my deathbed.

Downtown Portland

After a healthy and balanced breakfast, I decided to head to the Saturday market. The market is located right down the street from Voodoo Doughnuts and boasts 50+ booths of local produce, food trucks, and local artists displaying their crafts. Held on Saturdays and Sundays, get lost in the market's narrow segments and enjoy browsing the goods. If you continue across the street, you will find one of the better views of the Columbia River.

As you approach the gorgeous water and view, you can see the leaves beginning to change in true fall fashion. Besides the scattered showers, October is a beautiful time to visit Portland (above).

I am also obsessed with reclaimed wood, and the 1920 Shoppe had some fantastic pieces. I picked up a piece for my apartment that I may have embarrassingly squished into my small bag. Not even mad, just impressed.

Stumptown Coffee Roasters

Can we take a minute to laugh at the fact that this coffee shop has a drink that is literally the first and last name of my ex-boyfriend? Naturally, I ordered it and shared that information with the barista, who laughed and added an extra shot of espresso to it. See what I mean about these beautiful people? Stumptown Coffee is another famous joint to grab a cup of joe (and their chai was delicious). Other recommendations include Spella Cafe and Case Study Coffee Roasters.

Powell Books

Fun fact: I am a closet book lover. I could have spent an entire day in Powell's City of Books. It is one of the largest independent bookstores in the country and has rows upon rows of novels, travel books, and more. I restrained myself, and instead of buying 12 books, I just bought one called My Best Friend's Exorcism, mainly because it takes place in the '80s and has some weird sci-fi shit going on. A rare glimpse into the random selection of books I decide to read -- bizarre yet entertaining.


I will admit, I suck at vintage shopping. I do. Send me into an Anthropologie, and I can get the job done (which I did in Portland too...oops). Portland is home to some unique vintage shops and boutiques. Visit Billy Goat Vintage for some excellent clothing and trinkets. I picked up an incredibly unique bicycle skirt while I was there. Head to 10th Avenue SW as well for an entire street of boutiques to choose from, including Tender Loving Empire & Frances May.

Where to Eat

Along the same street (10 Ave S.W.), you will find a vast area full of food trucks. Do you have to go to this area, specifically? No way. Portland has the most food trucks-per-capita in the U.S. Grab a bite of Korean B.B.Q., some grilled cheese, or maybe a lamb kabob for low prices. If food trucks are not your style, try Portland City Grill (pictured below -- there's a fantastic panorama view of the city, and their happy hour is terrific), Thai Peacock, or Pazzo.

After catching happy hour at Portland City Grill (try the jambalaya!), I was tuckered out from the day and went back to the hotel to enjoy the comfort of a large bed and cable television.The next morning, I grabbed a quick breakfast before my flight at Mothers, as recommended by the lovely concierge. It was a last-minute switch from my initial destination of Bijou Cafe, which I was told is equally as delicious. The Tuscan scramble was out of this world, and the wait staff was amicable. This is another place to grab a table early. Thank goodness I was solo because the place was packed!

Concluding with the fact I am already planning my next trip there (as soon as I lose the 5lbs I gained from the doughnuts), Portland is a fabulous place to travel solo. I wish you all a wonderful trip to the Pacific Northwest!





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And in case you missed it, here is a quick video of my trip to further stalk my travels.



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