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.

A poster catches my eye: We Solve Murders. Another, a few feet away, says: Sonny Boy. Around the corner of the block, the letters for TRUST ME slant into the shape of a mushroom. 

The signs are all adverts for last year’s new book releases. They’re lined-up covers staring face-out of the glass windows that skirt Powell’s City of Books. I loop along the sidewalk, reading each title. The pavement seems to extend forever, past warehouse lights and brick walls, cafe stools and shelves packed with books. 

My inner bookworm couldn’t resist wriggling into Portland, Oregon, this weekend. Portland is a sprawling bookish city (indie comic book publishing thrives in this 145 square mile stretch of the Pacific Northwest, Beverly Cleary’s Ramona Quimby stories offer a playful little lens to view Grant Park, and Portland’s landmark hotel even has a library lounge).

Powell’s, the biggest indie bookstore in the world, is just one mainstay.

Sample A Chai Flight From Pip’s Donuts & Chai

When I was really little, I’d grasp my mom’s dupatta as she moved across kitchen tiles. I didn’t want to miss specks of green cardamom, cloves, and peppercorn rise like dust in a heavy mortar. As she crushed spices, flames licked the edges of a steel pot. Water boiled, then milk ballooned past the rim in the heat. My mom’s way of making chai in the early aughts carried a certain consistency. Her chai was just shy of creamy, smooth (from straining), frothy, and potent. 

I had forgotten about that childhood chai until Pip’s (named after Pip from Great Expectations). Pip’s flavors were different (zingy, with the savory undertones of a Thai curry), but the consistency of this busy Fremont Street shop’s chai flight pulled up memories. At 8 AM, Pip’s opened for business. 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.

Fact Check: Pip’s Original (founded in 2013) is often cited as the world’s first donut and chai shop. However, cafes in Matunga, Mumbai, have sold medu vadas (lentil donuts) and steaming cups of chai long before Pip’s, so, it is (more) likely that Pip’s Original is the world’s first (American-style) sweet donut and chai shop instead of the world’s first donut and chai shop!

Travel Tip:

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 Pip’s embodies its mantra: community over competition. Pip’s brings the blanket-hug feel of a homey, chatty, small-town cafe to the big, introverted city of Portland (population: ≈630,000). The chai flight (five drinks, each pour around 6 oz) is too big for one, so bring a friend to sip along (the mini-donuts I’m hoarding for myself, though).

Wander Through Powell’s City Of Books

When I enter Powell’s City Of Books at Burnside, the last dregs of chai (earthy and malty) still linger in my throat. I grab a bright red basket, pick up a map from the Green Room information desk, and wander through each corridor. 

Powell’s distributes three floors over four stories. If you’re a booklover, prepare for a blood-pumping bookish workout. You’ll slide spines in and out of shelves, pace up and down aisles, backtrack, stoop, crane your neck to scan titles, and wander past 3,000 subsections of books.  

On the shelves: classics and new releases, small press books and Pacific Northwest books, art journals and lined journals, escapist fiction and cozy horror and – 

I catch my breath.

Everywhere I turn, a staff pick card snaps into focus. How are there so many staff picks? 

Travel Tip:

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. The staff at Powell’s wants to help you find a good book to read (or gift to a loved one), so don’t hesitate to ask for personalized recommendations!

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, then, stretch your tastes by poring through Powell’s unique (often, hyper-specific) endcap displays.

In a rush to see it all, I miss Powell’s Rare Book Room. I miss the shelves of antiquarian books and the opportunity to view a Lewis & Clark journal (priced at $25,000).

My mistake? Assuming the Rare Book Room wasn’t publicly accessible. It is! Capacity caps at fourteen people, but you can freely visit Powell’s Rare Book Room after securing a pass from the Pearl Room information booth.

See The Shakespeare Garden

Outside, storm clouds part. Light seeps in, and I head to The Shakespeare Garden, a courtyard bordered by boxwoods and a single brick wall. A plaque quotes Emilia, a character from The Two Noble Kinsmen, a play co-credited to 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 heady rush of roses in the International Rose Test Garden. As I stroll the paths beyond, I notice that the 10,000 roses that fill the International Rose Test Garden haven’t yet flowered. Deadheaded and pruned bushes lie in empty lines. Wild, green leaves snake around archways and lampposts.

Travel Tip:

The International Rose Test Garden evaluates and breeds roses on a four and a half acre plot of land. When the hybrid roses are at their peak, the air holds the faintest scents of wine and tea and fruit. The first buds appear in May, but it’s June when most of the roses bloom in shades of pink, white, and red.

Free guided tours are usually available daily from Memorial Day to Labor Day (departing from the Rose Garden Store’s patio at 1:00 PM). So, if you’re planning a one day trip to Portland, know that summer is one of the best times to visit this city!

Eat A Comfort Meal At Rose City Book Pub

In 2018, Elise Schumock opened a bookstore bar with a few thousand used books and a tap list. She created a gathering space for book lovers, so unsurprisingly, Rose City Book Pub feels homey. As I wait for my order (poutine fries), a book club congregates around a long, worn table and debates the merits of a new romance release. More conversations about books spill from other corners of the pub. 

I stretch my legs, flip through a zine on the counter, and head outdoors to the patio. I’d love to read here on a sunny day, but the chairs are slick from rain. So, I take my first bite of fries indoors.

The poutine is hearty: thick-cut slices of potatoes, a pool of gravy, salty seasoning, and a heap of melted cheese. 

Travel Tip:

Rose City Book Pub is just one restaurant fringing Fremont Street, a road stretched out in Northeast Portland. If a fairy godmother granted me a return trip to PDX, I’d DIY a food tour in the nearby neighborhood of Beaumont (Rose City Book Pub is in the Sabin neighborhood, a short walk away).

In Beaumont, I’d try a fresh stroopwafel from Prince Coffee, a mini donut and chai (from Pip’s Original, of course), vegan ribs from Dirty Lettuce, and a single cheese plate (if time allows) from Blackbird Wine Shop. 

Check Into The Heathman Hotel

At 5 PM, I check into The Heathman, a downtown Portland hotel near Pioneer Courthouse Square, the Portland Art Museum, and White Bird. I drop off my carry-on in my room, then take an elevator downstairs to see the library.

The Heathman’s library is moody. 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. Protected behind glass are copies of Fifty Shades of Grey by E.L. James. This little detail, I wonder about for longer than I want to admit. So, I search on the interwebs, and learn that The Heathman features prominently in the first book (suddenly, the elevator holds a very different mental image).  

But it’s the autographed titles you’ll want to see. Over decades, The Heathman has curated a collection of books signed by award-winning authors. An early page of The Orchard Thief reveals Susan Orlean’s pretty penmanship. “With best wishes to everyone at The Heathman,” she wrote.

Travel Tip:

The hotel’s location is 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).

If you want to avoid valet parking and surge-priced Uber rides, centralize your itinerary to downtown, and take advantage of the city’s public transportation options and cycling paths. Bike racks punctuate sidewalks (The Heathman even provides complimentary bike rentals).

Biking is a great way to get to know Portland. 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.

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!