Solo Travel Guide to Portland, Oregon: Why Portland is Ideal for First-Time Solo Travelers
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Stumptown, Rose City, City of Bridges, Rip City, P-Town, PDX, Whatever you want to call it;
Portland, Oregon has completely stolen my heart.
I first visited Portland a few years ago during my very first solo trip, and though I’ve been back to The City of Bridges since then, that first solo trip always stands out in my mind.
Back in 2017 (while right smack in the middle of a very rough and drawn out breakup) I decided I needed to get away for a few days and started brainstorming ideas for quick solo travel destinations to places in the US that I hadn't yet experienced.
At the time I’d never given much thought to visiting Oregon, but when it popped up as a cheap round-trip option for December travel, I dove head first towards the idea of exploring the rainy hippie city on my own.
The thing about solo travel is that it has this great ability to force you out of your comfort zone and give you the kick in the ass that you need in order to learn about your own self worth and self sufficiency.
At the time, that drop kick of realization was exactly what I needed in my life, and Stumptown was a great first stop on my personal self-discovery journey.
Some of you might be wondering - out of all the places to solo travel, what makes Portland, Oregon so damn great? Allow me to enlighten you.
Portland is an introvert’s dream
Oregon’s damp and moody climate makes the perfect backdrop for some solo wandering and self reflection.
Though it’s easy to understand why many previous residents I’ve spoken with mention the inevitable melancholy that comes from living in an area with soooo much rain that’s offset with little sunlight, but if you’re looking for a cozy retreat where you can be a tourist in your own element and surround yourself with coffee, breweries, books, and the sound of rain - then grab your umbrella and take a tour through Portland’s downtown.
Personally, this was exactly the calm energy that I was hoping for on my first solo trip and PDX fully hit the mark.
Portland is a caffeine HUB
PDX has coffee culture down to a science, and discovering local drips around the city should be a must on your to-do list!
In 2012 the New York Times reported more than thirty local coffee roasters in the P-town area and that number has only grown within the last decade!
As a proud caffeine addict myself - thanks for keeping me buzzed, Portland.
No sales tax.
Um, hello! That’s just money kept in your pocket.
Stumptown is known for having some of the kindest drivers in the nation
I had heard about this driver courtesy phenomenon prior to my trip, but witnessing it first hand was shocking and HILARIOUS. I wasn’t used to it at all! I currently live in Denver and our drivers here are RUTHLESS. Anytime you attempt to merge onto the highway, good luck. Your life is in your own hands.
I quickly noticed that Portland drivers will immediately slow down and wave you over at the slightest sight of a blinker, maintain an EXTREMELY moderate speed on the freeway, and according to a few surveys - Portlanders have been listed as least likely to run red lights, honk at other drivers, or overall show aggression on the road!
The Airbnb I was staying at even had a book of Portland humor and the pages mentioning Portland drivers were spot on!
I apologies in advance for my questionable road manors, Portlandians….. Really. You've put me to shame!
Portlandians don’t pump their own gas
Funny story - on my first trip to Oregon I had no idea about the state’s gas station law and had never personally experienced one while traveling, but how I learned about it was hysterical! Well, it is now anyway.
I had pulled into a gas station somewhere outside of Astoria, Oregon and before I had a moment to get out of my car a guy in a black hoodie walked up to my door and asked “what do you want?”.
First of all, let me explain that this man was wearing ZERO attire that would have indicated that he worked at the gas station. I’m talking, NOTHING. He was decked out in all black, had long hair down to his ass, looked like he probably jammed out to Slayer in his free time (no judgement, dude. Respect.), and towered over my rental car.
After watching me blink at him confusingly, the assumed headbanger then asked me again “What can I get you?”.
At this point a was convinced that the guy was trying to sell me drugs (I’ve lived in some rough areas. In my mind it was a reasonable assumption) and I told him to get the f*** away from my car.
By now the poor misjudged man obviously got the point that I wasn’t from around there and tried to break it down for me in the slowest, most idiot proof way possible:
“In. the. state. of . Oregon. it. is. ILLEGAL. to. pump. your. own. gas. WHAT DO YOU WANT?!”
At this point I was beyond humiliated and apologized about thirty times to the poor guy for my moronic assumption. It’s safe to say that I tipped the hell out of him to try to make up for the fact that I now have to live with that humiliating moment for the rest of my life.
Long story short, don’t pull my mistake. Let the unassuming gas station men pump your gas. Also, tip them, because I’m sure they deal with idiot tourists like me regularly.
Friendly locals
Out of the handful of US cities that I’ve been to, Stumptown residents hold the trophy in my mind as some of the kindest strangers that I’ve had the pleasure to meet.
On my first solo trip to the area I had several experiences of locals coming up to me and starting conversations while I was dining alone at restaurants, chatty shop keepers eagerly giving me tips about the city, and kind baristas sharing directions and recommendations over an espresso.
Genuinely, these people blew me away with their hospitality.
Okay, enough with my key notes. Let’s talk about what YOU should do on your solo trip to the Rose City area.
Powell’s Books
Located in downtown PDX’s Pearl District, Powell’s City of Books is a bookworm’s literary wonderland and proudly reps the title of being the largest independent bookstore in the world!
Powell’s was my very first stop after leaving the airport and still remains one of my favorite places in all of Portland.
The literary aesthetic of Powell’s alone is enough to suck you in for hours, not to mention that the store itself takes up a whole block of downtown, consists of three stories, nine color-coded rooms (organized by genre), and even has a section for out-of-print books and hard-to-find titles.
One of my favorite sections is the Rare Book Room where they display delicately preserved autographed first editions and their top collectable volumes!
Portland’s Saturday Market
If you happen to be in the City of Bridges on a weekend, you should make a point to check out the Saturday Market at Tom McCall Waterfront Park.
Souvenir shops are overrated, consider buying your take homes from some of Stumptown’s small businesses and local makers instead! I LOVED wandering through the Saturday market and found plenty of locally-made crafts to bring back with me.
With nearly 400 local artists, vendors, and creators participating in the market annually, the selection is always rotating and stocked with handmade goods.
Tip: Even though the event is called the “Saturday Market”, it’s actually open on both Saturday AND Sunday from March - December, and remains open for the full week before Christmas during their annual “Festival of the Last Minute” event.
Downtown’s waterfront
Speaking of Tom McCall Waterfront Park, if you happen to visit the Saturday Market (or really if you find yourself downtown AT ALL), you shouldn't leave the area without walking through Portland’s bridge-lined waterfront at least once.
Decorated with rows of pink cherry blossom trees that face the Willamette River, Waterfront Park is a great place to grab a coffee and go for a scenic walk (or throw on some running shoes if you’re feeling active), view some of Portland’s most popular bridges, and (if you’re on the side facing Old Town) snap a picture of the famous White Stag sign!
Photo by Brendan Alex Phoenix: https://www.brendanalexphoenix.com/
Multnomah Falls
Technically this is outside of the Portland area, but if you’re up for taking a short thirty-minute drive away from the city, Multnomah Falls is a breathtaking experience that will easily become a main highlight of your trip!
While driving up to the falls you’ll also be able to catch incredible views of the Columbia River Gorge. THANKFULLY there are several jaw dropping pull off areas along the way where you can stop to snap some photos of the scenery.
Trust me, after driving past these views you’ll be dying to get out to get a better look for yourself.
Tip: While you’re at the falls, ask one of the locals about the princess legend and get some insight on the Naive American history in the area. It’s super interesting to hear and Multnomah’s princess legend is insanely romantic!
If you’re looking for other fun day trip ideas nearby Portland, check out my other post for suggestions on things to do at the Oregon Coast!
Where to stay in Portland? Follow the boutique-loving hipsters, obviously
In my not-so-humble and somewhat-of-a-know-it-all opinion; Portland has some of the coolest boutique hotels in the country. Plus, it’s one of the few US cities where when it comes to the hotel scene, you’ll have a harder time finding a hotel that’s NOT a boutique than the other way around, which as a die-hard boutique hotel fan myself, I feakin’ LOVE.
One of my favorite places to visit in Portland, whether to stay or to pop up and use their rooftop as my own make-shift office,is the Society Hotel. The Society Hotel is designed with a uniquely minimal-yet-timeless aesthetic that merges old-word hostel charm with modern amenities and design components that cater to digital nomads, solo travelers, and world explorers from all walks of life.
Bonus - it’s also affordable as hell. With prices that start at $95/per night for a private room and $55/per night to sleep hostel style; the Society Hotel feels incredibly hard to beat when it comes to both price and value.
Even though the Society is my personal choice; I get it, everyone wants to know all of their options. Below are a few other Portland hotels in varied price ranges that have also made my favorites list, and stand out among Portland’s ever-growing hotel crowd:
Where to eat in Portland
Pine State Biscuits
During both times that I’ve visited Portland, Pine State Biscuits was my go-to breakfast spot for at least one morning of each trip.
Being raised so close to the south, I’m a sucker for anything that reminds me of soul food and southern hospitality, and Pine State’s owners (all being North Carolina natives) have done an amazing job at bringing that warm country feeling into their restaurant concept.
While their most popular items are understandably their biscuit sandwiches, my personal favorite thing on their menus is the Hash Ups! I like to add steak and sautéed mushrooms to mine for some extra flare. They’re INCREDIBLE.
An added bonus of Pine State Biscuits is that they also have a full bar! And staying true to their southern roots, many of their house cocktails are whiskey based, which was perfect for this particular whiskey fanatic.
If you’re in the mood for more of a breakfast-style cocktail, the house bloody Mary is also a great option. They even have a drink called the Queen Mary, which comes with a corndog garnish and a bacon straw!
Voodoo Doughnuts
Because Voodoo Doughnuts is so popular in Denver, prior to visiting PDX I was wrongfully under the impression that it was a Colorado based franchise. When I got to Oregon I quickly learned that these funky-decorated doughnuts actually originated in Portland!
Normally I’m a die-hard loyalist to the Mango Tango doughnut, but Voodoo recently came out with a new concept called the “Cannolo” which is basically the soft baked love child of a doughnut and a cannoli (obviously, bakery genius at its finest).
So far the cannolo is fighting hard to take the Mango Tango’s place in my heart, and honestly, I’m not even ashamed of my polyamorous pastry love triangle. As their slogan says: “The magic is in the hole”.
Really.. That’s their slogan.
Did I just make that weird? Perfect. Let’s move on.
Food Cart Pods
Okay, besides all of the incredible restaurants that the city has to offer, Portland’s food cart scene is a foodie experience of its own.
These food cart “pods” are a collection of food carts that are spread out in certain designated areas around the city and surrounding neighborhoods, and they’re a huge hit with the locals! After checking out a few of the carts for myself, it’s no shock as to why.
With options ranging from Ethiopian, Greek, Chinese, Mexican, Thai, American, AND many others that I’m sure I’m forgetting to list, Portland’s food pods are full of fast, inexpensive, and drool-worthy varieties to munch on.
My top pod of choice is the Greek gyro cart at the Fifth Avenue Pod.
Resources:
If the idea of exploring the city entirely alone still feels a bit unnerving, how about checking out a guided tour?! Even though I love venturing through a city on my own terms, sometimes a guided tour can add a fun spin to a specific experience. And most times you’ll learn a hefty dose of local facts that you may have missed out on otherwise!
Below are a few local tour options in Portland based on the activities mentioned above. To look through other available tours in the city, check out VIATOR.
