Touching down at Portland’s sparkling new PDX Airport, I immediately sensed this wasn’t a standard West Coast gateway.
Timber finishes, art-filled spaces and even the cult-favourite PDX carpet announced Portland’s character: creative, inclusive and proudly weird in the best possible way.
This is no stopover city; it’s a destination that deserves centre stage.
(Above): Luke goes bargain hunting
Alberta Arts & “Just One More”
After checking into Cascada, a fresh and leafy hotel filled with local art, I skipped the spa for the Alberta Arts District. Murals, indie shops and a beer garden called Conscious Sedation set the tone.
Dinner at Terra Mae (Portuguese-Japanese fusion with duck skin butter!) introduced the catchphrase of the trip: “just one more.”
What started with a nightcap at Radio Room spiralled into a late-night party at Donnie Vegas, where locals folded us in like regulars. Naturally, we were back the next night.
Mt. Hood Missteps
Breakfast at Aussie-owned Proud Mary Café delivered hash browns worth writing home about (plus a cheeky jar of Vegemite spotted behind the counter).
Then off with First Nature Tours to Mt. Hood, still cloaked in snow in May. Timberline Lodge, a rustic star of The Shining, was cinematic, though my RM Williams boots turned me into slapstick entertainment on the ice.
A wine tasting at Stave & Stone ended the day, though not before our bus’s exhaust pipe fell off. In true Portland fashion, nobody blinked.
Downtown Quirks & Karaoke
At the elegant Sentinel Hotel, I felt transported to Portland’s grand past. A walking tour revealed the Benson Bubblers: bronze drinking fountains designed to keep loggers hydrated (and out of the saloons) back in the day.
Downtown is also alive with street art, with murals splashed across walls and alleys that feel like open-air galleries reflecting Portland’s creative spirit at every turn.
Lunch was at Hawthorne Asylum, a food truck pod where Portland’s history shows up in unexpected ways. One cart had been built into the nose cone of a United Airlines DC-8 that crashed decades ago. It looked closed when we visited but still stood as a quirky reminder of how this city repurposes even the strangest pieces of its past.
Interactive art playground Hopscotch stole my heart with neon tunnels, giant mushrooms whispering secrets and a ball pit for grown-ups.
That night, Jeju delivered sizzling Korean BBQ and soju before agents proved their karaoke chops in a private room.
Markets, Gardens & Timber Joey
Saturday meant Portland Farmers Market: bacon sizzling, coffee brewing, berries glowing. The market yielded treasures, including a ring made from recycled skateboard decks.
Washington Park offered serenity at the Japanese Garden and the International Rose Test Garden, a reminder that nature thrives right inside the city.
Lunch? A cheesesteak at yet another food truck pod, plus a truck devoted entirely to dog treats.
An emergency Costco stop for a hearing aid repair barely slowed me down before Aviation Gin. Ryan Reynolds’ “Desk of a Humble Genius” was as cheeky as the tasting was smooth.
That evening, Providence Park throbbed as the Portland Timbers played. Timber Joey revved his chainsaw and sawed off slabs of log for each goal. The chants were colourful. The atmosphere electric.
Trolls, Vines & McMenamins Mayhem
Breakfast featured Danish pancake balls at Broder Söder. Then we tracked down Ole Bolle, Portland’s giant forest troll, before embracing Oregon’s tax-free shopping at Washington Square Mall.
Lunch at Ponzi Vineyards was elevated by sweeping views and Pinot Noir. Ziplining at Tree to Tree left us exhilarated (and in my case, nearly dropping a water bottle that made others think I’d fallen).
McMenamins Grand Lodge was pure Portland eccentricity: hidden bars, vintage art, secret hallways.
The day turned surreal when a CVS pit stop delivered a Robert Irwin sighting, a lovely bloke whose mum’s family is from Oregon. Dinner closed with marshmallow decadence at Toasted S’mores Bar.
Donuts & Farewell Books
The Lost Plate Coffee & Donut Tour was a sugar-fuelled sprint: maple-bacon, cereal-topped, custard-filled and old-fashioned classics paired with coffee strong enough to wake the dead. By stop three, we were rolling down the sidewalks.
Our final essential: Powell’s City of Books, a block-long temple of literature. The Rare Book Room, filled with centuries-old treasures, was worth the pilgrimage.
I squeezed one last Portland history book into my luggage before discovering that PDX Airport shops match downtown prices, one last chance for “just one more” purchase.
Final Thoughts
Portland is more than roses, books and bridges. It is markets where skateboard decks become rings, parks where trolls lurk in forests and distilleries where Ryan Reynolds pokes fun at himself.
It is a city where inclusivity, creativity and spontaneity shine, and where even a CVS run can turn into a celebrity encounter.
For travellers, it is unforgettable. For travel agents, it is gold: dog-friendly, people-friendly, endlessly marketable. Portland is not a pit stop; it is the destination.
A heartfelt thanks to Travel Portland, United Airlines (for the comfort of the SFO lounge!), and First Nature Tours for making this famil extraordinary.
Portland, you have stolen my heart and yes, I would go back for “just one more.”
