Craft beer, delicious food, and keeping it weird; If any of those grab your attention you’re going to like Stumptown aka Portland, Oregon. The vibe of this city is something that needs to be experienced. With a long history that involves people being shanghaied, famous brothels and fountains that supposedly flowed with beer, every street corner in Portland has a unique story.

You could spend weeks eating and drinking your way through Portland and deep diving in the bizarre culture that has engulfed the city, but let’s take a look at what you can cram into a long weekend.

Pre-Game your Travels: McMenamins Kennedy School 

I never count the travel days in our itineraries but if you happen to fly into Portland and want to get the party started right away, head to McMenamins Kennedy School.

If you aren’t familiar with McMenamins, let me fill you in. McMenamins had the genius idea of converting run-down buildings in the Pacific Northwest into bars, hotels, and restaurants in order to preserve the structure’s history. The fun part of this setup is they restore the building as it was and then just add alcohol to the equation.

The Kennedy School is an old 1915 Catholic elementary school smack-dab in the middle of a Northeast Portland neighborhood. McMenamins converted several areas of the school into bars. My personal favorite is the Boiler Room, which you may have guessed, use to be the boiler room. This room is 2 stories and has hundreds of pipes running in all directions. There is also a bar in the old detention room which is worth popping into. While you’re taking a look around the school, make sure to check out all the creepy paintings and pictures of old students. The photos of the triplets will be sure to make you uncomfortable in fun way.

If you’re traveling through Bend, OR check out the McMenamins Old St. Francis School.

Quick Tip: According to AllTheRooms, the average price of a hotel, Airbnb, etc. in Portland is $126 per night. Plan it right, and a weekend in Portland can be super affordable compared to bigger west coast cities like Seattle or San Francisco.

3-Day Itinerary for Portland

Day 1

Stumptown Coffee

Start your day the right way and get some local coffee at Stumptown Coffee Roasters. Stumptown has a neat story. They buy their coffee beans directly from the farmers of Latin and South America. No middle-man distributor,  no processing, no machining, these farmers rely on traditional methods to bring the beans to table.

Underground Portland Walking Tour

Now that you got a caffeine buzz, it’s time to get moving. As I mentioned earlier Portland has some almost unbelievable history and it’s often difficult to tell what is an urban legend and what is factual. To get the real scoop on things, take the Underground Portland Walking Tour. This is not your typical “look how great my city is” tour. If you want your boring history lessons, pick up a textbook. If you want the gritty, in-your-face history of Old Portland take this tour.

You’ll learn things like the legend of the secret Shanghai tunnels. Sailors were forced to sign a contract, Ruthied and then taken through these tunnels for a new life of forced labor in international waters and many other shady happenings in early days of Portland. I won’t spoil whether these tunnels are real or not, but I can tell you, you will get an answer by taking this tour.

Voodoo Doughnuts

If you have never had a Voodoo Doughnut, I feel bad for you and you need to change that immediately. Go there immediately after your walking tour. They have the best doughnuts, end of story. Ignore all the flannel-wearing hipsters who tell you that they have gone mainstream and Blue Star Doughnuts up the street is better. If you want a bagel pretending to be a doughnut take that advice but you should never take advice from smelly hipsters. Go to Voodoo Doughnuts, don’t ask questions, just do it!

Ground Kontrol

Now that you have had your fill of early history,  let’s jump forward in time to when pinball machines ruled the scene. Ground Kontrol is a mecca for vintage arcade games and pinball machines. Add to the fact that they have a full bar inside, and it is very easy to lose a few hours here.

Huber’s Cafe

Stumptown Coffee was good this morning, but you know what it is missing?  Fire, alcohol and a little showmanship. Make your way to Huber’s Cafe and experience a Spanish Coffee. Coffee mixed with Kahlúa, light it on fire, give it a long pour for a little razzle-dazzle and top with some cream. Huber’s makes a damn good cup of coffee.

Kelly’s Olympian

Finish off the night with a drink at Kelly’s Olympian. Don’t let the big scary bouncer intimidate you, although this has a reputation as a biker bar, everyone is super friendly. The inside walls are lined with old neon signs. Turn your gaze upward to see classic motorcycles and model planes hanging from the ceilings.

Day 2

International Rose Test Garden

Day 2 involves a lot of Portland’s favorite pastimes, eating and drinking. To balance the day out start the morning with some light exercise, namely walking around Portland’s International Rose Test Garden. Deep within Washington Park lies a rose garden on steroids. Over 500 different varieties of roses are spread throughout the garden. You don’t need to know a single thing about roses (I sure didn’t) to appreciate the beauty of this place.

Pittock Mansion

Close by the Rose Gardens lies a fancy house on top of a very steep hill. This piece of luxury is Pittock Mansion. Built in 1909, this mansion was created with a fortune made by the publisher of the Oregonian Newspaper, Henry Pittock. Let me tell you, Henry had some style. Through a self-guided tour, you can venture through all kinds of rooms throughout the house. Take note of what was considered to be “futuristic” showers (which look more like torture devices) and the kitchen with its ceramic ovens.

Salt and Straw

Let the feasting begin! There are a few places every resident of Portland will tell you to eat at when you visit. One of those places is Salt and Straw, makers of some of the most unusual yet tasty ice cream flavor. Salt and Straw only uses local and seasonal ingredients to makes its flavors, basically turning a scoop of ice cream into a work of art. Flavors like Strawberry Honey Balsamic with Black Pepper or Pear & Blue Cheese seem to be strange combinations, but know that these guys know ice cream so if they make it, you better believe it tastes good. But if you’re not feeling adventurous, you can always play it safe with Cinnamon Snickerdoodle or Chocolate Gooey Brownie.

Bridgeport BrewPub

Take a visit to Oregon’s Original Craft Brewery, The Bridgeport Brewpub. Portland’s’ microbrew revolution began out of this warehouse so it’s only right that you have a beer here to pay homage to the wake craft brewing that was created thanks to these guys. It probably doesn’t need to be said but the beer is amazing and the food here is equally as good.

Rogue Brewery and Distillery

If you’re a fan of beer, especially dark beer or hoppy beers, look no further than Rogue Brewing. You’ll see Dead Guy Ale in just about every store but it’s not every day that you get to experience all the other suds they brew. Work your way from a 4 Hop to an 8 Hop ale, one beer at a time or get weird with a Chipotle Ale or Sriracha Hot Stout. They also distill their own whiskey if you are not a beer drinker.

Day 3

Multnomah Falls

The best cure for a hangover is a little fresh air. Go outside the city today and get you some nature. Get the day started early and drive to Multnomah Falls. This gorgeous waterfall is the tallest in Oregon. Photographers flock from all over the work to take the classic postcard photo you will see plastered in gift shops around Portland. You can hike to the top of the falls but the best views are right at the bottom.

For more on the hike visit our trail guide.

The Columbia River Gorge

After you get your fill of waterfalls head back towards Portland and make a pit stop at the Vista House. Climb the stairs of the small museum for an amazing view of the Columbia River Gorge. Parking here is a bit of a nightmare so just be prepared for crowds and old grumpy parking attendants.

Multnomah Whiskey Library

Finish your trip with a celebratory whiskey. But don’t just choose any bar, choose the whiskey bar to end all whiskey bars, the Multnomah Whiskey Library. They have thousands of whiskeys from all over the world and your bartender will make recommendations based on your personal preferences. If you have ever wanted to feel like a high-rolling mob boss in the roaring 20’s this is the place for you. Just be prepared to wait 4 hours for a table. I won’t necessarily say it is worth exchanging your precious vacation time waiting around, but at least through your name in and see if Lady Luck is on your side and you can get in quickly.

Overall

Portland is a fantastic place to spend a long weekend. You could literally just spend the whole time drinking and eating and be perfectly happy. Indulge your inner fat kid and just go for it. While you stuff your face, learn about Portland’s little known history and appreciate the unique culture.

Still Hungry? Check out these other grub hubs:

• Deschutes Brewery
• Little Big Burger
• McMenamins Zeus Café

If you have any questions or comments let us know below!

Chad Albright

Chad can be summed up by his idea of a perfect day: Waking up early to watch the sunrise over the mountains, warm cup of coffee in hand then grabbing his camera and fly rod, hitting the trail to explore some uncharted territory followed by cold beers and campfire steaks. Chad is often joined on his adventures by his wife, Tori, and their dog, Kona.