A few years ago, if you’d asked me what came to mind when I thought of Portland, I would have said hipsters with beards, craft beer, and bikes. And although craft beer and bikes are an important part of Portland culture, it’s not just for hipsters! On my first trip there, I discovered that there are many awesome things to do in Portland.

With Portland now on Lonely Planet’s list of 10 best cities to visit in 2017, it’s definitely going to be on many travel radars next year. Read on for Portland travel tips, and to find out about the essential Portland attractions for first timers! Bonus: you don’t have to grow a hipster beard to enjoy what Portland has to offer.

First things first: How do I get to Portland?

Hit the road! Go by car

I live in the Vancouver area, so driving to Portland was the easiest way for me and my travel buddies to get there. But be warned! Between border lineups and nasty traffic snarls around Seattle, our five hour drive turned into eight hours before we knew it. I unwittingly volunteered for the driving shift that took us through the worst of Seattle traffic, and since it was my first time, I was completely unaware of the express lanes that would have made our trip faster.

Portland skyline and river
Sunsets on the Willamette River make for gorgeous views of Portland

If you’re heading down for a weekend in Portland, it’s a good idea to plan out your route to avoid the worst of rush hour, and to keep an eye out for the express lanes. Avoiding rush hour might mean a hideously early start to your road trip, but it’s worth it to stay out of Seattle traffic!

If you’re renting a car to visit Portland, check these 5 car rental & insurance tips before you drive off to the City of Roses.

All aboard! Go by train

If you want to get to Portland from the Vancouver area, but don’t have a car or the inclination to fight traffic on the I-5, why not go by train? Amtrak offers daily service between Vancouver and Portland. The journey is a little bit longer taking just over eight hours, but all you have to do is sit back, relax, and enjoy the beautiful west coast scenery. I’d recommend this option to people who are looking to spend more than a weekend in Portland. Since the train journey takes longer, you want to make sure you have enough time to explore!

Fasten your seat belts! Go by air

If you’re visiting Portland from further away, not to worry! Portland has a thriving international airport, with excellent transit connections to downtown.

I’m here, now what? Staying in Portland

Even if you’re only spending the weekend in Portland, accommodation can be expensive, especially around downtown. Most hotels cost $200 USD or more per night! This can easily break the bank for many budget-conscious travellers, and could keep you from experiencing the best of Portland’s attractions.

However, Portland has a thriving Airbnb community, which can fit a thriftier travel budget. To save even more, try looking for accommodation outside of the downtown core. There are many awesome neighbourhoods just across the downtown bridges. We went the Airbnb route on our trip to Portland, and for the price of a hotel room, managed to score an entire basement suite, complete with a full kitchen, laundry machines, and complimentary beer in the fridge!

Getting around Portland

Bikes, bikes, and more bikes

The rumours are true – Portland is a huge cycling community. At every street corner, a rainbow of parked bicycles competes for rack space, and rush hour often seems to include as many bicycles as cars. Not only is biking an eco-friendly and heart-healthy form of transportation, it’s much quicker than hoofing it, which means you can hop between more iconic Portland attractions in one day. Make sure to stop off at some of Portland’s awesome craft breweries and restaurants to replenish the calories you’ve burned while cycling.

Cyclists on a Portland bridge
Why not try a cycling tour on your next Portland trip?

A great way to experience the city by bike is to go on a bicycle sightseeing tour. Pedal Bike Tours and Cycle Portland offer several different sightseeing packages, depending on which parts of Portland you’d like to explore. If you’d like to explore on your own, Waterfront Bikes provides rentals by the hour, or daily.

But don’t stop your cycling adventures at Portland! Learn more about how bikes can make your travels even more fun!

These shoes were made for walking

If I’m being perfectly honest, although I find cycling fun, I can be a little bit dangerous when perched behind the handlebars of a bicycle. My cycling days were limited mostly to my early childhood, and I’ve lost a lot of the finesse required to avoid calamity.

Fortunately for me, the same qualities that make Portland ideal for cyclists also help make it a very foot-friendly city. There aren’t a lot of steep hills to climb, which makes it walkable for people at all fitness levels. Most of the bridges that connect to downtown have foot paths, which is great if you’ve scored a sweet Airbnb accommodation across the river. I found the sidewalks to be unusually empty for a city of Portland’s size, likely because most people were on bikes. In my opinion, Portland is a very walkable city, and I’d traipse through the streets again in a heartbeat.

Ride the MAX

Like many cities, Portland has a light rail system. It’s called the MAX (Metropolitan Area Express), and it’s a quick and economical way to get around. A regular fare will set you back $2.50 US, and it’s good for two and a half hours wherever the MAX travels.

A MAX train in downtown Portland
The MAX is the perfect way to hop between Portland attractions

If you’re planning on seeing more than a few Portland attractions in one day, a day pass is only $5.00 US. The MAX also connects Portland to the airport, and other cities like Hillsboro, Beaverton, Clackamas, and Gresham.

Catch a lift with Uber

If you’re not into biking, another option for hopping between things to do in Portland is to catch a ride with Uber. Although Portland does have taxi companies, my travel buddies and I found it quicker and cheaper to use Uber. It was actually my first time using this service, and I was surprised by how easy it was. Our drivers were knowledgeable about what Portland has to offer, and one of them even educated us on the finer points of excellent barbecue.

Things to do in Portland


If you like festivals, pick a weekend, any weekend, and there will likely be a festival of some kind happening in Portland. My buddies and I picked a weekend at random, which happened to be exactly when the PDX Cider Summit was scheduled. I love craft cider, so this was the perfect festival for me. Needless to say, I had an excellent time, and got to try interesting ciders from around the world!

cider festival attendees with building in the background
The PDX Cider Summit in Portland

Find out what’s happening in Portland right now, and attend an unforgettable festival!

Enjoy local craft beer and cider

Portland is known for its craft beer, and with good reason. Not only is Portland home to a lot of great local breweries, it seems to be a hub for craft beers from around the globe. Many of the pubs offer a wide local selection, as well as options from further afield.

Portland’s proximity to Washington’s orchards also makes it a fabulous place to sample cider from America’s Pacific Northwest.

Here are some of the places that we visited that are a good choice to wet your whistle:

  • Bailey’s Taproom: a downtown bar featuring 26 rotating taps of craft beer and cider. Very friendly, and a great place to meet and chat with other “beer geeks.”
  • Hair of the Dog Brewing Company: a Portland brewery featuring unique and unusual beer styles. It has an industrial vibe and good food. I recommend the pan-roasted brussels sprouts as a snack.
  • Deschutes: a well-known brewery. We visited the bustlingly busy brewpub in downtown Portland, which has excellent food. They’re very proud of their gluten-free menu there, and brew their own gluten-free beer.
  • Apex: a beer-only bar with a huge patio and 50 beer taps. It’s great for sampling beer from many different breweries.

apex bar portland

The bathrooms are also covered in excellent graffiti, and drawing on the bathroom walls is certainly encouraged.

  • Reverend Nat’s Hard Cider: a unique cidery and public taproom featuring 12 dedicated cider taps. We hit up this place after the PDX Cider Summit, and chatted with Nat and the staff. They were very friendly, and ordered pizza for everyone in the place!
  • Groundbreaker: a dedicated gluten-free brewery with a gastropub location in Portland. The entire menu is gluten-free, which meant that I could order anything I wanted!
Groundbreaker sign and sandwich with coleslaw
Everything at Groundbreaker was 100% gluten-free and 100% delicious!

This was a new experience for me, and it wound up being one of the best meals in my entire life! I also enjoyed a flight of their delicious gluten-free craft beer.

Of course, it can be easy to get carried away in the craft beer capital of the world, but take steps to drink responsibly during your time in Portland and see why travel insurance and alcohol don’t mix.

After sampling so many tasty beers and ciders, we wanted to bring some home to enjoy! The grocery stores in Portland are allowed to sell alcohol, so we were able to easily cross off many items on our list. But before you cross the border with a trunk brimming with Portland brews, it’s important to know how much you can bring back into Canada, and how long you have to be in the US before you’re allowed to bring alcohol back without paying duty.

Sample the cuisine

As impressed as we were by the awesome selection of craft beer and cider, I also found that the food in Portland did not leave any empty space in our stomachs. Many of the pubs we visited offered full menus of delicious food, as well as snacks. It wasn’t unusual for us to spend the afternoon over a couple of pints and a mile-high mountain of nachos (made with local cheese, of course). Since Portland has a bit of an “alternative” vibe, we found cuisine to suit and intrigue any palate. Here are a couple of the favourites:

One of Portland’s mainstay attractions is Voodoo Doughnut. This iconic confectionery is known for it’s unusual and sometimes completely off-the-wall doughnuts, featuring candy, breakfast cereal, and even bacon!

Voodoo Donuts, Portland Oregon

Although Portland has two Voodoo Doughnut locations, the lineups can be absolutely insane. You may wish you’d brought a doughnut to munch on while waiting for your doughnuts!

If you can’t make it to Voodoo, don’t despair. Blue Star Donuts has a few more locations around Portland, and features intriguing flavours like blueberry bourbon basil and lemon poppy buttermilk. The selections change seasonally, so make sure you chow down on your favourites while you’re there.

Another culinary attraction in Portland is Pine State Biscuits. This extremely popular restaurant chain features buttery Southern-style biscuits and gravy, as well as biscuit sandwiches and other Southern treats. These can be washed down with locally roasted coffee, or an interesting cocktail or two. For my friends who go to Portland frequently, this restaurant is a must-do, and high on their list of recommendations for first-timers!

Of course, no trip to Portland would be complete without a visit to one of the city’s many food trucks. At any given time, there are over 500 food trucks operating in Portland! To make it easy to find them, most of the food trucks are organized into “pods,” and their locations are updated regularly. You can even download an app to make sure you find all of your favourite food trucks on your Portland adventure.

Things uniquely Portland

Powell’s City of Books

Many people think that craft beer is the heart and soul of Portland. But for bibliophiles everywhere, the true heart and soul of the city is Powell’s City of Books. Powell’s is the largest independent new and used bookstore in the world. Stepping into Powell’s for the first time, I was overwhelmed by the sheer size of the store (and possibly by book fumes as well). Despite acres of bookshelves, it’s surprisingly easy to navigate if you’re looking for something specific. All the sections are colour-coded, and there are maps and helpful staff members everywhere. Since it was my first time, I preferred to roam the store at will, making sure to visit the rare book room.

Powell’s bookstore at night
Don’t miss the opportunity to visit Powell’s, the largest independent bookstore in the world!

Powell’s doesn’t stop at books though. If you’re looking for games, souvenirs, journals and notebooks, or even funny socks, they have that too! I parted with considerable cash and a few hours by visiting Powell’s, and emerged onto the streets of downtown Portland in a dizzy, happy daze of verbiage.

Ground Kontrol Classic Arcade

Have you ever been to a two-story bar that’s full of video games and pinball machines? Because I hadn’t before I visited Portland! Ground Kontrol is not only a place to hone your pinball skills, it’s a full-service bar and restaurant. Some of their games date back to the 70s, in case you’re looking to relive your childhood. Their décor is even game-themed, right down to the Pacman tiles in the bathroom.

Enjoy the local art

Portland is a city that attracts artists, and some would say that the city itself is art! An interesting mixture of old and new, industrial and decorative, Portland’s architecture is as varied as the residents themselves.

Restaurant covered in art
Art is everywhere you look in Portland!

The shops and cafes are absolutely bursting with local art, and the Portland Art Museum is the oldest art museum on the west coast.

Watch out for quirky laws

Did you know that it’s against the law to pump your own gas in Oregon? It’s true! The law is actually a throwback to the early days of automobiles, when incorrectly pumping gas could result in a fire, or even an explosion! Despite huge advances in safety, Oregon is reluctant to let go of the law, mostly because of the employment opportunities it creates. The fine for breaking this law is $500, so if you’re fuelling up after a weekend in Portland, remember to sit back, relax, and let the attendants do the work!

If you thought that Portland is only for foodies, you’ll be surprised to learn that Oregon’s gateway has some of the best trails, parks and gardens for nature lovers. Check out the list of best natural landmarks in Portland, curated by Lonely Planet.

Travel Insurance for Portland, Oregon

Before you take off on your next Portland adventure, don’t forget to pack travel insurance (even if you’re going for a short weekend trip). It’ll help you travel more confidently, knowing that you’re protected in case of any food and health related mishaps in Portland. If you’re travelling to Portland in winter, travel insurance can also protect you in case of trip interruptions and delays due to the weather and flight cancellations.

With so much to do (and eat), the city definitely won’t disappoint. Use these tips and suggestions to plan your perfect Portland escape. I won’t be surprised if you start making plans to move there permanently by the end of your trip!

What are you looking forward to most on your first trip to Portland? Have any other recommendations from your travels there? Share with us in the comments below.

Happy travels!

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