I Tried Visiting Portland In One Day – Here’s What Happened

Here’s how I spent one day in Portland. Plus, six Portland travel tips I wish I knew.

Every year, I add Portland, Oregon, to my travel wishlist. I slip in a bullet point about Powell’s because I love bookish places. So, when I realized Seattle (where I was staying) was just three hours from Rose City, I thought this is it. Now is the time to make my dream day in Portland a reality. 

Rain fell hard on that plan. But I stubbornly (perhaps to a fault) insisted on continuing with my one day in Portland itinerary. A good friend pointed out that the best way to see Portland, as a first-time visitor, is not by car, but by bike, and that (as she gently put it) was my first mistake (I agree). 

In 2022, Portland was named the second-best biking city in the US, and it’s still one of the top cities for cyclists. Lesson learned: Grab a bicycle, a helmet, and pedal your way through Portland, Oregon (on a bright, sunny day).

My inner bookworm was determined. She doggedly ignored the rain and wheeled into this sprawling bookish city in a car. After all, Powell’s, the biggest indie bookstore in the world, is a must for book lovers (according to many years of reader-submitted emails, messages, and DMs). 

Nothing went according to plan, but I tried (my best) to spend a day in Portland doing things I loved (visiting a library lounge, a Shakespeare Garden, and a book pub). And I did get to see Powell’s, which was a dream come true.

Grab A Donut For Breakfast In Portland

When I first arrived in Portland, I knew I wanted a donut for breakfast. Portland isn’t the donut capital of America (it’s not even one of the contenders), but Portland markets its donut scene well—Voodoo, in particular. Voodoo was founded in the early aughts, but remains Portland’s most talked-about donut shop thanks to its wildly-named flavors, bubble-gum pink packaging, and brief (now, decades-old) NyQuil donut stint (the FDA did not approve, but news coverage gifted Voodoo with its own Blarney Stone. Everyone who heard the story gabbed about it). Later, Blue Star Donuts arrived, and the conversations shifted to Blue Star versus Voodoo (but donuts in Portland were still talked about).

I visited Pip’s Original (named after Pip from Great Expectations). Scents of cinnamon and sugar drifted from the counter to an adjoining room, where friend groups and families plopped plates of golden, browned mini-donuts (some Nutella-drizzled and others, topped with a creamy, fruit compote) on tabletops. I ordered a chai flight (five drinks, each pour around 6 oz) too (Pip’s chai is zingy, with the savory undertones of a Thai curry). 

A trio of kids sang Happy Birthday to their mom, who blushed in front of a sky blue wall painted with clouds. At Pip’s, you get a dozen free donuts on your birthday (here’s how). It’s one little way the cafe embodies its mantra (community over competition). Pip’s brings the blanket-hug feel of a homey, chatty, small-town shop to the big, introverted city of Portland. It’s a place that invites you to slow down and linger, but I did none of those things. In a too-rushed effort to check off every box on my Portland bucket list, I downed my chai like shots, listened to Funny Story by Emily Henry on 2x speed back on the road, and headed off to my next destination.

Lesson two: Double the time you spend at each location on your one day in Portland itinerary by half. It takes a while to crisscross this 145 square mile stretch of the Pacific Northwest.

Wander Through The Biggest Indie Bookstore In The World

By 10 AM, I arrived at Powell’s City Of Books. I had heard many times that Powell’s was a big bookstore, but it didn’t hit me how big of a bookstore Powell’s was until I picked up a map (there’s a map!) from the Green Room information desk.

Powell’s distributes three floors over four stories. If this is your first time visiting Portland, block out a few hours (two, at least) to check out the Burnside location. Powell’s at Burnside occupies a whole city block. One million books reside within this flagship shop, so find your comfort genres (among the 3,000 subsections), then stretch your tastes by poring through Powell’s unique (often hyper-specific) endcap displays. 

Despite its size (68,000 square feet of floor space), Powell’s still operates as an indie bookstore: notes are handwritten, underrated stories are uplifted, and events are community-centric. Lesson three: The staff at Powell’s wants to help you find a good book to read, so don’t hesitate to ask for personalized recommendations (to make your Portland day trip even more memorable)! 

Visit The International Rose Test Garden

Bookshopping is one of the coziest ways to spend a stormy day in Portland, but at the first hint of light, I headed to The Shakespeare Garden, a grassy courtyard bordered by boxwoods and a single brick wall. A plaque quotes Emilia, a character from The Two Noble Kinsmen, a play co-authored by John Fletcher and Shakespeare. 

“Of all flowers, methinks a rose is best.”

Emilia, Two Noble Kinsmen

The Shakespeare Garden was designed as a gentle respite from the International Rose Test Garden (a four-and-a-half-acre plot of land dedicated to evaluating and breeding roses). But as I strolled the paths beyond The Shakespeare Garden, I noticed that the 10,000 roses filling the International Rose Test Garden hadn’t yet flowered. Deadheaded and pruned bushes lay in empty lines. Wild, green leaves snaked around archways and lampposts. I visited too early (or perhaps, too late).

Lesson four: Summer is the rosiest time to visit Portland. In May, the first buds appear, and by June, most of the roses bloom in shades of pink, white, and red. When these hybrid roses are at their peak, the air holds the faintest scents of wine and tea and fruit, welcoming you to Rose City. 

Try Portland’s Drink Scene

Portland is known for two drinks: coffee and beer. Breweries and coffee houses act as third spaces in Portland, a city with over 80 coffee roasters [source] and 80 breweries, and a variety of coffee and beer fests (SheBrew is the one I’m noting down for a future visit). 

I hopped into Rose City Book Pub during my Portland day trip. In 2018, Elise Schumock opened a bookstore bar (Rose City Book Pub) with a few thousand used books and a tap list. She created a gathering space for book lovers.

As I waited for my order (a comfy bowl of poutine fries), a book club congregated around a long, worn table and debated the merits of a new romance release. More conversations about books spilled from other corners of the pub. 

I loved the cafe-meets-pub style atmosphere of Rose City Book Pub (it’s the perfect addition to a bookish trip and a place I’d happily revisit), but if I could re-do my Portland day trip, I’d focus on trying just one aspect of Portland’s drink scene. Lesson five: If this is your first time in Portland, visit a roastery (Coava, Push X Pull) or a brewery (Little Beast Brewing Garden, Wayfinder). 

Check Into A Hotel In Portland

At 5 PM, I checked into The Heathman, a landmark Portland hotel with an iconic library lounge (picture: a teardrop chandelier, leaning ladders, dark corners of shelves encasing thousands of books, and armchairs that look like they’ve been pulled from a cocktail lounge at 2 AM). 

The hotel’s location was convenient, but valet parking in downtown Portland is more expensive than in most cities. At The Heathman, valet parking is $55 a night (since I booked during shoulder season, this equaled half the room rate).

Lesson six: If you want to avoid high valet parking rates, centralize your one day in Portland itinerary to downtown (or a neighborhood of choice), and take advantage of the city’s public transportation options and cycling paths. Bike racks punctuate sidewalks in Portland. And The Heathman even provides complimentary bike rentals!

Did you find this one day in Portland travel guide helpful? How would you spend 24 hours in Portland, Oregon? Let us know in the comments below!