If the Pacific Northwest were a slightly dysfunctional family, then Vancouver would be the first-born golden child that made millions funded by sweet Chinese investor money, Seattle would be the serial entrepreneur of a middle child that jumps from one coffee-inspired project to another, and Portland would be youngest sibling that never got much attention growing up, but blossomed into a creative, quirky free spirit that’s universally adored in its own way.

At least, that’s the way I see things, having completed the trio with my long-long-weekend trip to Portland last year. Perhaps nothing sums up the City of Roses better than the “Keep Portland Weird” slogan, which accurately captures its identity as a place full of things that are cool, unusual and a little crazy.

Naturally, the city demands of its visitors the utmost effort in absorbing as much of the city’s “weirdness” as possible, and over the course of four days, we did our best to play our part.

1. “Keep Portland Weird” Sign

No place better to start than the physical embodiment of the slogan itself: bright yellow letters on an anthracite brick wall, around the back of Dante’s on the corner of SW 3rd and W Burnside. Grab your selfie, take a step back in the parking lot, and internalize the message of maintaining the enigmatic sanctity of the city around you. Better yet, go for a walk around the block and find some nibbles and nosh to help you wash that message down…

2. Portland Saturday Market

As the name might suggest, on Saturdays you’ll find the largest continuously operating open-air crafts market in the United States here along the banks of the Willamette River – but it’s actually open on Sundays as well. Why would it be called a Saturday Market? That’s just how things kind of work around here, I guess.

You’ll get to browse through aisles upon aisles of distinctive pieces and items, all handmade by hardworking craftspeople from all over Oregon and Washington. From ceramic garlic graters to textured wooden balls that make beautiful patterns when rolled in sand, there’s a wealth of surprisingly creative craft products tempting you to buy.  

Speaking of temptations, the Saturday Market is an early opportunity to dive into Portland’s renowned food-cart culture. There’s dozens of carts and booths to tickle your fancy, from artisanal jams and spreads to artery-clogging “elephant ears” – Oregon’s delightful version of funnel cakes and beavertails.

3. DONUTS!

“Donut culture” is one of the many gastronomic cultures that thrive here in Portland, and as you turn the corner from the Saturday Market, you arrive at a veritable institution of the famous toric treat: Voodoo Doughnut, famed for its kooky decor and glam pink donut boxes.

Some might say that no visit to Portland would be complete without a bite into one of Voodoo’s creations, but if you ask the locals, many of them might tell you to skip the long queues – mostly composed of the Instagram crowd, who arguably came more for the glamour than the glaze – and head to competing Blue Star Donuts instead. That’s what Jessica and I did, although admittedly it leaves me with a bit of unfulfilled curiosity on Voodoo. Oh well, something to leave for next time.

4. Craft Beer & Restaurants

Donuts are certainly worth getting excited about, but craft beer and delicious food are what take Portland’s gastro scene to the next level. The former is indeed one of the city’s specialties, and Jessica and I dropped by the Deschutes Brewery Public House with some local friends for a taste of the craft beer scene. After ordering their classic sampler of five different craft brews, we each picked one we liked and persisted with it for the next pint, or three…

That’s minor league stuff, though. If you truly want to get your pub-crawl on, I can’t think of a better idea than Prince of Travel reader Atom’s suggestion of jumping on a BrewCycle – a tandem bike that sits up to 12 people and allows you to pedal your way across town from pub to pub (with the steering thankfully done by a sober ringleader). Portlanders love their beer and their bikes, after all, so how’s that for living it up like a local?

In-between drinking sessions, don’t forget to try some of Portland’s amazing restaurants as well. Pok Pok was a Thai spot that came up many times in our recommendations, and we loved their chicken wings. They have a shop and a cart east of the Willamette, and that can be a good opportunity to walk through the relatively unexplored eastern part of town. 

Other recommended hotspots, that we alas must leave for next time, included Screen Door, Ned Ludd, and Grassa. Instead, we headed to the Alder Street Food Carts, the largest collection of food carts in Downtown Portland serving up anything you happen to crave. Pho, tacos, grilled cheese – as long as it can be whipped up in a matter of minutes, you’ll likely find that the carts here on Alder Street are quite eager to please. 

5. International Rose Test Garden

Take a break from all that pure consumption and stop to smell the roses. The International Rose Test Garden boasts over 10,000 rose bushes and makes for an exceptionally tranquil place to wander through on a sunny morning to start your day.

Especially between April and October, when the roses are in bloom and the sun is shining, the beauty inherent in Portland’s official nickname as the City of Roses is on full display. 

6. Nob Hill Alphabet District

Make your exit from the rose garden to arrive at NW 23rd Ave, a key road that runs north-south through the inland part of town. Walk north a little while and you’ll arrive at the Nob Hill Alphabet District, so named because the east-west roads in this area all have rather funky names that start with the letters from A to Z. 

In keeping with the usual pace of the city, most of the establishments in Nob Hill are independent enterprises with plenty of character and a penchant for the artistic. You’ll find the flagship store of the aforementioned Blue Star Donuts here, as well as Salt & Straw, an ice cream shop that’s made a name for itself even outside of Portland. More casual eateries, such as Little Big Burger and Pepino’s Mexican Grill, are also peppered into the street scene. 

Tiny outlets peddling handmade souvenirs, trinkets, and crafts are also a dime a dozen along this stretch of NW 23rd Ave. If you’re the type to duck into stores like these just to look around, then you can expect to lose several hours here doing exactly that. 

7. The Freakybuttrue Peculiarium

Part museum, part house-of-horrors, and 100% Portland in a nutshell, the Freakybuttrue Pecularium is guaranteed to leave an impression. Located at the northern end of the Nob Hill Alphabet District, this hodgepodge collection of kitschy oddities designed to shock, startle, and confuse. 

The items in Freakybuttrue might be described as particularly dastardly Halloween props meets demon-possessed arts and crafts, but ultimately only a visit to the museum yourself can help you make sense of it. Admission is $5, although “decent costumes and pets” get in free, so you might wish to dress the part.

8. Powell’s City of Books

How weird would it be for there to be a sprawling bookstore occupying an entire city block located smack dab in the middle of downtown? Well, weird is what Portland does best, and Powell’s Books has been fulfilling that role in its 68,000 sq ft flagship store – the City of Books – since 1971.

Regularly topping “best bookstores” lists around the world, Powell’s is the place to be if you’re the studious type. Hole up in one of the nine colour-coded sections of the store, grab a few books that catch your eye, and simply allow the day to slip by. Better yet, head to the top floor to read in the ambience of the Rare Book Room, a beautifully appointed space that’s dedicated to the most valuable titles in Powell’s collection. 

9. Multnomah Falls

After indulging in all the guilty pleasures that the city has to offer, it’s time to get out of the concrete jungle and explore the scenic Columbia River Gorge region, a hugely popular destination for day trips among the locals. Renting a car will be most efficient, but otherwise, there are regular buses operated by Columbia Gorge Express that will bring you out there as well. 

Multnomah Falls is the star attraction in the area, a 30-minute drive from the city limits. The waterfall’s height is more impressive than its roar, with the vertical cascade breaking into rather wispy strands as it reaches the bottom of the 611-foot plunge.

Nevertheless, climbing the short distance up to the picturesque Benson Bridge still makes for quite an exhilarating view, and it was a shame that the walking trail to the very top of the falls was cordoned off due to the wet season – I’m sure the views of the headwaters would’ve been quite a sight to behold.

There’s plenty of other things to do in the great outdoors of Oregon as well. You could venture to the nearby Wahkeena Falls, a shorter and wider younger sibling of Multnomah’s, or head further east to the Cascade Locks, where a quaint little town and scenic Marine Park would make for a cute afternoon out. Then there’s also Rooster Rock State Park, where you can pass the time among the park’s many beaches, walking trails, and picnic areas.

10. Mill Ends Park

Alternatively, if you don’t have the time to head out into the country, you can also set a course for the corner of SW Taylor St and the SW Naito Parkway on Portland’s waterfront. There, you’ll get to enjoy the lush green landscapes of Mill Ends Park… apparently the smallest park in the world. 

I mean, what screams “Keep Portland Weird” more than this? Originally developed into a “park” because the space that was meant for a light pole became overgrown with weeds, Mill Ends Park is a tiny circle that’s 2 ft across and home to a single tree (that purportedly gets stolen all the time and needs to be replanted on a regular basis). 

Stop in the median as you’re crossing the street here, bear witness to the verified Guinness World Records holder sitting right before your eyes, and carry on with a chuckle…

11. Priority Pass Hopping

And last but not least, make sure to head to PDX a few hours early before your departing flight, because you won’t want to miss out on all the fun with Priority Pass you can have at the airport. How much fun exactly? About US$168 per person’s worth.

That’s right – there are three separate airport establishments at Portland International Airport that will each give you US$28 off your bill if you’re a Priority Pass cardholder. Better yet, you’re allowed (and even encouraged) to register a guest when you visit, even if you don’t actually have a guest travelling with you.

That brings your net allotment to US$56 off your bill at each of the Capers Cafe Le Bar, the Capers Market, and the House Spirits Distillery.

The two Capers locations sell ready-to-go food and drink as well as non-perishable items like artisanal spreads and spices made by local producers, so you don’t need to consume hundreds of dollars worth of food – you can buy some delicious Oregon treats to bring home with you.

Meanwhile, the House Spirits Distillery is a first-of-its-kind airport tasting room, where you can take advantage of their US$28 sampler flight to get a good buzz going before your departure.

And the best part? If you are travelling with a companion, and they themselves have a Priority Pass membership as well, then each of you can use up the full US$56 allowance by designating each other as guests. Yep, you know it – US$336 in free food and drinks!

Conclusion

The Pacific Northwest holds a special place in my heart, and a visit to Portland to find out what the “weirdness” was all about had been long overdue. I had a lovely time getting to know the City of Roses and all of its quirks – with the Freakybuttrue Pecularium, Powell’s Books, and the outstandingly vibrant bar and restaurant scene leaving deep impressions – and I know it won’t be long until I’m back in town to discover yet more new things to eat, drink, look at, and laugh about.