By Jon Shadel
The thought of it might make you squirm: navigating mass transit by yourself, eating on your own and going out alone. But anyone who’s done it knows nothing opens you up to the world like traveling solo.
Whether you’re an experienced backpacker or on your first independent trip, Portland seems like it was tailor-made for single adventures. Distinct and walkable neighborhoods reveal their character in trending eateries, indie shops and busy brewpubs. Nature blends into the fabric of the city with countless acres of parks and miles of hiking trails. And the laidback social scene and generally friendly locals means you’re never truly alone — unless you want to be, of course.
As a solo traveler, you’ll find that the city’s marquee attractions appeal to you as much as they do to couples, families and groups — Powell’s City of Books, the Portland Saturday Market and so on. But you’ll also want to get off the beaten path and seek out locals’ favorite watering holes, single-friendly restaurants and up-and-coming neighborhoods to explore. Here we offer tips for how you can make the most of Portland by yourself.
Nothing opens you up to the world like traveling on your own. Photo by Matt Quinn.
First, let’s dispel any doubts lingering in your mind about solo travel. Consider these obvious selling points: With no one else to please, you can spend days doing exactly what you want to do — or put differently, discovering what you really enjoy doing when no one else is around. Whether you spend hours boutique browsing, cafe hopping, trail running or aimlessly exploring, the decision is yours to make. If there’s a better way for you to find yourself, we can’t think of one.
And just because you’re traveling on your own doesn’t mean you’ll spend your entire trip alone. In fact, many travelers consider their solo journeys the most social. With no friends to keep you occupied, you naturally immerse yourself in your surroundings — striking up conversations in a coffee shop, seeking dining suggestions from a bartender, finding new friends on a tour and making the most of the night.
More than 80 miles of trails and paths wind through Forest Park. Photo by Mike Rohrig/Flickr.
When we’re with travel companions, many of us approach new destinations with a rushed, check-it-off-the-list mentality. But if you really want to get to know Portland on your own, dedicate time to exploring its eclectic neighborhoods, where you’ll discover the city’s contrasting personalities. Like in other metropolitan regions, the neighborhood you call home influences your identity, and you’ll find distinct communities in each quadrant. A few neighborhoods you won’t want to miss include Division for trending eateries, Hawthorne for bohemian charm, West End for boutiques and low-key bars, and Alberta Arts District for indie shopping.
Something that sets Portland apart from many other major cities is the immediate access to nature, including urban forests, manicured gardens and picnic-worthy green space. For a wild escape, hike more than 80 miles of trails and paths winding through Forest Park, the nation’s largest urban wilderness. The Forest Park Conservancy offers maps, directions and other helpful resources. The “City of Roses” draws garden enthusiasts from around the world to the International Rose Test Garden, where you can stroll among some 7,000 blooming bushes. In sunnier weather, the city’s many parks are idyllic spots for whiling away an afternoon; we suggest you grab some grub and have an impromptu picnic.
One way to explore the city’s top attractions and meet some other travelers is on a guided tour, which can vary from typical to one-of-a-kind. Portland Walking Tours offers a wide range of neighborhood and interest-specific tours to choose from, and the guides receive positive reviews from visitors who appreciate their humor and knowledge of the city’s history. Coffee-lovers can take a deep dive into the local bean scene with Third Wave Coffee Tours. And beer lovers jump on the BrewCycle to pedal between breweries and dive bars. (Check out a few more of our favorite guided tours here.)
Beyond these ideas, you’ll want to include a few of these popular spots on your itinerary too: Powell’s City of Books (the largest used and new bookstore in the world), Portland Saturday Market (largest continually operated outdoor market in the United States), Voodoo Doughnut (O.K., they are just donuts, but it’s still a fun experience) and Pittock Mansion (historic French Renaissance-style château with stunning views of the skyline).
The fear of eating out alone — it’s nearly universal but completely irrational. Sure, few solo travelers want to enter an upscale restaurant and ask for a table for one. But there are different, and more social, ways of eating your way through a city you don’t know. Here in Portland, where nearly every eatery skews casual, you’ll find plenty of raved-about spots for each meal — and loads of snacking in-between.
Start with brunch at the old school Fuller’s Coffee Shop (136 N.W. 9th Ave.), a counter-style diner serving American classics. Regulars have been coming here for decades, and they’re a pretty friendly bunch. For lunch, head to the nearest food cart pod and chow down on some of the best street food you’ll find anywhere. Dinner presents a wide range of restaurants with open bar seating, where you can grab a seat and order off the full dinner menu (without having to share). A few favorites include: the bar and pizza counters at Nostrana (1401 S.E. Morrison St.), ramen bar Boxer Ramen (multiple locations), sought-after chef counter seats at Le Pigeon (738 E. Burnside St.), handmade pasta at Grassa (1205 S.W. Washington St.) and upscale burgers and booze at TILT (1355 NW Everett St.).
Here are a few more tips for eating alone in Portland: Generally speaking, you won’t have too much trouble finding solo dining spots. Many of the city’s top restaurants have bar seating, and many bars also serve excellent food. If the prospect of sitting alone still freaks you out a little, consider bringing a book or magazine. Oh, and take this as an opportunity to be bold and try something new — that’s the point of your trip, isn’t it?
The Dandy Warhols perform at the Doug Fir. Photo by Stephanie Neil/Flickr.
When it comes to going out, Portlanders tend to keep things low-key, which means the city’s nightlife scene is easy to navigate on your own. Sure, you can head to some sweaty clubs to dance like no one’s looking — you’ll find plenty to choose from. But live music halls and cinemas dominate the late-night offerings, which are inviting venues for solo travelers. (Check out our guide to partying like the locals here.)
Whether you’re venturing out on your own, or hanging out with newfound friends, head to one of the city’s top-notch live music venues to take in the vibrant music scene. The city’s rich history of independent-minded artists includes many notable acts, and you’ll often find them playing hometown shows alongside up-and-coming talent. These venues routinely host buzzed-about shows: Wonder Ballroom (128 N.E. Russell St.), Mississippi Studios (3939 N. Mississippi Ave.), Doug Fir Lounge (830 E. Burnside St.) and Crystal Ballroom (1332 W. Burnside St.).
Going out to see a movie may not seem the most exhilarating late-night activity, but Portland’s obsession with cinema makes our theaters must-see attractions — and it’s a fun way to spend a night out on your own. The city boasts dozens of theaters and hundreds of screens, but you’ll want to head to one of many brew ’n’ view theaters for a truly one-of-a-kind experience. These theaters, ranging from sticky to swanky, all serve up craft beers and fresh fare with each flick: Bagdad Theater (3702 S.E. Hawthorne Blvd.), the Kennedy School Theater (5736 N.E. 33rd Ave.), Hollywood Theatre (4122 N.E. Sandy Blvd.) and Living Room Theaters (341 S.W. 10th Ave.).
MAX light rail trains in downtown Portland. Photo by Tony Webster/Flickr.
Many first-time solo travelers tend to express fear of navigating a city they don’t know, especially public transportation. But you shouldn’t be afraid of riding the train or taking the bus in Portland. Sure, you have plenty of other options: You can rent a car for day trips, easily hail a rideshare from your phone, zip around in Car2Go or rent a bike to see the sights, but it’s hard to beat the ease and convenience of the city’s world-class mass transit.
To help you get started, here are a few things you should know about our public transportation system. It’s one of the cheapest ways to quickly move across town. You can purchase a single Tri-Met ticket for $2.50, which is valid for two and a half hours of travel on the city’s bus, light rail (locally known as the MAX) and streetcar lines. (We suggest you download the Trimet Tickets app to use your phone as your pass.) Second, it’s a friendly, reliable and safe system to navigate. You can find maps and schedules for the bus and MAX here and for the Portland Streetcar here. If you prefer to use your phone’s GPS, Google Maps typically provides reliable transit directions and schedules, but it’s always a good idea to double-check Trimet for any system delays.
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