Portland, Oregon: Blazing a trail in the Pacific Northwest

By: Dave Gunner

April 17, 2019

photo Sean Pavone at Shutterstock

The coolest city in the most stunning location. Here's why Portland should be on your must visit list.

Heading into the city along Highway 26, I felt like I’d known about Portland, Oregon for years. A fabled city in the Pacific Northwest. A bohemian hipster hangout. It had certainly piqued my interest. Now, driving into town after the most epic road trip down the Washington State coast, I was baffled. It was all docks, flyovers and bridges. This industrial landscape was not what I was expecting. But first impressions can’t always be relied upon, and it didn’t take me long to fall under the spell of the Rose City.

Portland, Oregon, has always attracted the curious and adventurous. Even as a frontier town, long before its name was decided on the toss of a coin, people flocked here – first as a stepping stone to the gold rush, and then to cut and ship timber. But in recent years the industrial hub has given way to a creative one, and Portland has evolved into one of the USA’s coolest cities. Yet amazingly, that is only half the story. The other half is about location, and Portland is as much about what you can do just outside the city as what you can do within it. And it’s this combination of culture and setting that make it such a fabulous place to visit.

Art, art and more art

Combining three of the cities great loves; bikes, music and art. Portland remembers Bowie and Prince with super cool cycle path art. Photo by Jonathan Maus/

In Portland, art is everywhere. On the streets, in small independent shops, or gracing the windows of high-end galleries. There’s a museum of art, ancient art, classic art, native American art and very modern art. Even the bike lane markers and city litter bins have been turned into works of public art. There’s also a vibrant performing arts scene, with world-class opera, symphony orchestras and theatre companies.

Books, bread, beer, bands and bridges

This list of ‘Bs’ might be all you need to know before booking your ticket to Portland. The city claims the biggest bookshop in the world and is home to more breweries per capita than anywhere else on earth, with almost as many ways to experience them. Beer tours here take place on foot, by bike, by party bike, in a group on a boat or on individual tours. As for Powell’s Books, a handy map helps you navigate the colossal store, which sells second-hand books as well as new releases.

Both books and beer are celebrated in annual festivals. The Oregon Brewers Festival returns in July at the Tom McCall Waterfront Park and is the largest gathering of independent brewers in North America. Later in the year, there’s the Portland Book Festival in November – an excellent month to be curled up indoors with a book, especially in this inclement part of the world.

Portland’s music scene is big news too. The city that gave us acts as diverse as the Dandy Warhols, Pink Martini and Elliott Smith is also home to an eclectic line-up of summer festivals. Highlights include the annual Waterfront Blues Festival over the Fourth of July Weekend, and The Quiet Music Festival of Portland, a low-key event where you’re encouraged to fall asleep to soothing, hushed sounds in a “tranquil cave of sonic serenity”.

We love a good city bridge here at Ruby (check out our post on Manhattan’s finest specimens) and Portland has some magnificent structures spanning the Williamette River: 12 to be precise, and that’s just in the metropolitan area. Quite a few are walkable, including the famous Burnside Bridge that connects downtown Portland to the Central Eastside and is home to the famous white stag. The iconic neon-and-bulb ‘Welcome to Portland’ sign is one of the most recognisable landmarks in the city.

Breadmaking and baking are also prominent Portland pastimes, and this is reflected in a diverse range of bakeries across the city. With several locations across town, Blue Star Donuts use locally sourced ingredients to make a range of doughnuts ranging from the traditional to the contemporary. Try a classic Mexican hot chocolate ring sprinkled with cayenne and spices, or a Cointreau crème brûlée doughnut filled with creamy vanilla custard then hand-torched. Other highlights include Ken’s Artisan Bakery – known for its outstanding sourdough – and Saint Cupcake, whose sweet treats almost qualify as art.

Crafts, coffee and cannabis

With no sales tax, Portland is a great place to shop. The city is full of quirky craft emporiums, vintage stores and independent boutiques, and everywhere you go something weird and wonderful will draw you in. In the Mississippi neighbourhood is Paxton Gate, a self-described “natural history museum where everything is for sale”. Looking for a giraffe skull? Or a table lamp in the shape of an octopus? This is your place. Or head to The Meadow, a shop that specialises in salt. It’s more fascinating than it sounds and well worth a visit: You can stock up on giant blocks of pink Himalayan sea salt, salted chocolate, shot glasses made of salt, and extraordinarily good popcorn cooked in black truffle sea salt.

After pounding the streets, you’ll need a coffee. Stumptown is the famous local brand but the coffee scene is continually evolving – with over 40 roasters in the city, you’re never going to run out of new things to try.

But this is Portland, so it’s not just coffee. It’s all about the ‘third wave’. We’re talking notes, flowers and single varietal beans, or triple filtered, 12-hour steeped cold brew. The list goes on. And that’s before it’s served with nitrogen, chocolate or spices in any number of different containers, or used to make shakes and doughnuts, or combined with oats and nuts in cookies, or paired with alcohol to create coffee cocktails. And of course, there are plenty of coffee crawling tours and shops where you can learn the art of coffee making. Here in Portland you can take a step towards becoming an expert barista, and in this town that makes you a rock star.

When cannabis was legalised in Oregon in 2015, it was pretty obvious that Portland would embrace this new opportunity. Since then, boutique dispensaries have sprung up all over town, as have weed tours of the city. Even if it’s not your thing, a visit to a dispensary is time well spent, if only to learn about this fascinating plant and the infinite ways you can buy and consume it. It’s not just about getting high, it’s also about cannabis oil’s many therapeutic effects. Find out more and get to know the dos and don’ts of cannabis in Portland.

Day trips

Spectacular Cannon Beach, just a short drive from Portland

If there’s anywhere on earth that offers better day trips than Portland we want to know about it. A couple of hours driving can put you in the mountains, on a world class beach, on a walking trail in a forest, relaxing by a fast-flowing river, or in Oregon’s high desert – real cowboy country. The nearby Tualatin Valley, between Portland and the coast, offers wine tours, farmers markets, nature trails for biking and hiking, river rafting and golf.

You can ski in the morning and surf on ocean waves in the afternoon. Spend some time spotting elk, bear and whales and visit temperate rainforest with gigantic trees. And if you’re pressed for time, you don’t need to go far to experience the natural beauty of the area. Just adjacent to the city is Forest Park, a vast area of unspoiled woodland with more than 80 miles of trails, as well as spectacular views across the city towards the mountains. This is the Pacific Northwest in all its glory: wild, lush and magnificent.

Oregon Helicopters do a fantastic range of flights starting at just $49. As well as an amazing experience it’s a great way to get a better understanding of the city layout and geography.

Ethical eating

The city takes its responsibilities to the planet seriously and nowhere is that more evident than in its restaurants and cafes. Portlanders like to know the provenance of what they’re consuming. Seasonality is equally important. Micro-production is huge here, as is using locally sourced organic ingredients. Over the years this way of life has attracted like-minded people who’ve brought along a willingness to experiment and helped give Portland its progressive vibe.

Whatever you fancy for dinner you can probably find it: The city is heaven for veggies and vegans, and just about every national cuisine is represented, whether in Michelin-starred fine dining establishments or the famous food courts dotted around the city. If you’re eating on the go, streetside food trucks sell an eclectic mix of culinary delights, where even vegan junk food is a thing.

Life is rosy

We’ve already mentioned book, beer and music festivals, but the biggest, brightest and sweetest smelling celebration of them all is the annual Rose Festival in June. It takes place over several days at the start of the month, culminating in a spectacular grand floral parade. The festival stems (sorry) from the city’s 120-year-association with roses, and the inaugural event took place in 1907 when the Rose City Park neighbourhood was formed.

The International Rose Test Garden, where new rose varieties from around the world are evaluated, was established in 1917 and soon after Portland became known as the City of Roses or Rose City.

The Japanese Garden, said to be the best example outside of Japan.

Getting about and green spaces

Getting around the city is a breeze, with a super-efficient transit system including a streetcar line. It’s also a great walking and cycling destination, and with the city divided into straightforward quadrants, navigation is easy.

Under two miles from downtown is Washington Park, which has enough to keep anyone occupied for a couple of days. As well as lovely walking trails and Oregon Zoo, the park is home to the tranquil Japanese Garden, said to be the best example outside of Japan. The Rose Test Garden is right next door, home to more than 550 varieties of roses and a real delight in summer. To explore further afield you will need a car, but parking is generally easy and affordable, and the spectacular drives make it more than worthwhile.

Huge thanks to Kieron Widner of First Nature Tours who showed me around the city. He shared his passion for and deep knowledge of Portland, and also persuaded me to try stilton and pear ice cream (it was amazing).

The famous sign on Burnside Bridge welcomes you to downtown, signifying the good times that await on the other side of the river. The sign has evolved over the years having been used as an advert for sugar and sportswear. The current sign was born in 2010.


To get to Portland, fly to Seattle with Virgin Atlantic, then take an easy three-hour drive south. Alternatively, enjoy an adventurous road trip through the scenic Olympic Peninsula west of Seattle, visiting Olympic National Park and its emerald-green Hoh Rainforest along the way. You can follow the beautiful Washington coastline, stopping off at Ruby Beach and Cape Disappointment en route, before heading over the state border into Oregon at the handsome city of Astoria. Carry on down this misty stretch of coast towards Cannon Beach, known for its monolithic sea stacks, then turn inland for the final stretch towards Portland. You can also fly direct from Heathrow between May and October with our partner Delta Air Lines.

Visit the TravelPortland website to find out the latest on upcoming events and new openings.

Dave Gunner

Dave Gunner

I love telling the story of our people, our planes, our places and our planet through Ruby Blog.

Categories: Our Places