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If you’re brave enough to venture out on your own, you want to get the destination right.

Solo travel has soared to new heights over the past decade to the point most people aren’t made to feel cringey by being asked, “don’t have you have anyone to go with you?”.

Albeit some still don’t quite grasp the new norm of embracing solitude, whether it be traditional backpacking across Europe or jet-setting across America’s own awesome cities.

Heck, one of my favorite Instagram accounts to follow is eatingalonediaries, where a New Yorker explores the Big Apple one plate at a time dining alone.

While it’s long been more societally tolerable to jet off by yourself to far-off bucket-list destinations, taking solo trips in the U.S. has carried a stigma likened to the dreaded “table for one?” question.

Oddly enough, my latest solo trip has me convinced I found the top solo trip destination in America; a city of self-proclaimed weirdos that couldn’t care less if you’re asking for a table for one, going for a scenic hike with just your AirPods, or if you’re spending all day reading a book in a coffee shop and never leave.

Portland, Oregon: Where Everybody Is Somebody

Leaving my hotel room ready to explore a new city, it was almost instantaneous I realized there’s never a dull moment in Portland, Oregon.

I’m talking drag queen shows taking over food truck parks, dreadlocked hippies vibing to impromptu donut shop concerts, line-out-the-door burlesque shows, and blue-haired bookworms reciting slam poetry in vacant lots.

“Welcome to Portland” is what I told myself. Despite traveling to many cities solo, truth be told, there’s always a faint fear of being judged that creeps up in my subconscious — but not here.

Not after roaming the city for probably 15 minutes simply scoping out dinner only be to struck by a sense of nostalgia remembering why I moved to Austin, another ‘weird’ city that unapologetically accepts anyone and everyone.

Portland is home to all walks of life and I mean that in a good way despite the city’s notorious homeless issues and questionable decriminalization laws in recent past.

Solo travelers will always find something to do no matter where you lie on the introvert-extrovert spectrum.

I consider myself an introverted extrovert some days, and others an extroverted introvert, but any way you slice it, I had no issue biding time no matter how high or low my social battery was.

I enjoyed waking up to Portland’s renowned coffee scene by trying a new cafe each morning like local favorite Fuller’s and perusing an endless maze of books at Powell’s City of Books, the world’s largest new and used bookstore that even has a secret ‘Rare Book Room’ upstairs.

Conversely, late-night bar-hopping was fun to experience too, especially hidden basement bars like Shanghai Tunnel Bar.

Travel Tip: For fellow coffee lovers, check out Portland’s Downtown Coffee Crawl where ‘coffee is the new wine’.

Portland Is What Austin Used To Be

Remember when Austin had a small-town feel? Back in the good ol’ days, the Texas capital thrived on its quirkiness and proud entrepreneur-driven independence, but now the city has lost much of its ‘Keep Austin Weird’ vibes, essentially becoming Dallas 2.0.

Portland has held the same moniker: “Keep Portland Weird”, except they’ve done an exceptionally better job than Austin.

I remember when I moved away from Austin, my favorite food truck park was bought out and replaced by a new apartment complex, but if there’s one thing Portland isn’t lacking it’s food trucks; they’re everywhere!

Ranging from coffee stands to tacos to incredible Asian and Middle Eastern cuisine, the options are endless.

Portland has no shame being weird. You’ll find off-the-wall murals giving new life to barren buildings to people commuting by unicycle, and let’s just say you never know what type of performances will be on display at Dante’s — ‘Karaoke from Hell’, anyone?

If there’s one thing Portland and Austin are still completely aligned on is it’s an outdoor lover’s dream and the ultimate foodie destination ranging from new daring menus to classic institutions like my favorite of my trip, Dan & Louis Oyster Bar, serving up the same recipe for Oyster Stew since it’s inception.

Getting Around: As a solo traveler, taking Portland’s easily navigable TriMet trams is the best way to explore downtown and other ‘weird’ districts like Mississippi Ave, where normalcy is frowned upon.

Portland’s Springtime Bliss: Waterfall Hikes & Cherry Blossom Blooms

Having experienced the last remnants of Portland’s frigid winter, Oregonians’ notorious flannel shirts were in full force.

What I missed out on were cherry blossoms illuminating the cityscape and waterfall hikes on nearby trails.

There’s no need to venture off to Japan for the perfect Instagram shots when they’re right here in a well-connected U.S. city as cherry blossoms begin to bloom in late March and well into April.

But if Tokyo is on the brain, you could visit the Portland Japanese Garden at Washington Park, a sprawling urban park with staggering pines and fun attractions like the Oregon Zoo.

As for waterfalls, anyone rocking a flannel shirt or driving a Subaru will tell you the Columbia River Gorge is the go-to spot.

Encompassing Wahkeena Falls, Latourell Falls, and Multnomah Falls (Oregon’s tallest waterfall), venturing outside the cityscape is well worth a day trip into Portland’s lesser-known nature trails.

If you visit Trail of Ten Falls (Silver Falls State Park), you can walk behind the falls for even better photo ops.

While the trek is relatively easy, if you prefer to be guided, check out The Waterfall Shuttle starting at $79.

Travel Tip: Don’t sleep on Oregon’s version of Napa. Beautiful Williamette Valley is just 48 miles from Portland, offering over 700 wineries across 150 miles of scenic landscapes!

Sam Sears

Sam, our Lead Writer & Journalist based in San Diego has visited 30 countries and written over 400 articles with a focus on sharing his own travel experiences and shining a light on lesser-known gems.

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This article originally appeared on TravelOffPath.com

Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.

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