Surrounded by breathtaking natural beauty, Portland, Oregon is a funky, outdoorsy, foodie town. From mouthwatering cuisine to heart pumping hikes it’s easy to spend a weekend (or many!) here. After your well-planned weekend getaway to hit all the main sites, you’ll immediately want to plan your return to explore even more of this amazing city.
Where to Stay
Portland can be described as broken into quadrants and within those quadrants there are districts. Downtown is a great, central location to base yourself for exploring the city or a hike outside the city limits. Popular boutique options include Hotel Lucia, The Nines and Ace. We booked our trip pretty last minute and ended up staying at the Courtyard Downtown since it was about half the price of the boutique hotels. Our room was very strangely configured, with our bed right at the door when you entered the room and then a ton of dead space in front of the bathroom. It made for noisy nights of hearing the neighbors opening and closing their doors as the hopped from room to room (wedding party). If I had to choose again, I would have splurged to stay at The Nines or Hotel Lucia.
How to get around
Unless you want to make your way out of the city for a hike or two, which I highly recommend, you don’t really need a car to get around Portland. Depending on your mood and preference you have many options for getting around the city. Portland’s public transportation system is extensive and can get you to within walking distance of all the major areas of the city. If you fancy riding a bike, numerous options for bike rental shops and Nike’s Biketown bike share program provide an easy way to do like the locals do. One word of advice, make sure you brush up on your bike riding rules and feel comfortable riding in car traffic. Walking around is also a great option if you prefer a way to work off all those calories you are likely going to be eating and drinking. And if your legs get tired and you don’t have the patience to wait for a trolley or bus Uber and Lyft are always an option.
What to Do
Battle of the donuts
We devoted 2 out 3 breakfasts to battle out the two heavy donut hitters in town, Voodoo Donuts and Blue Star Donuts. Each is unique in their own way. Voodoo is oozing kitsch and massive, out-there-in-flavor, dessert like donuts. Surprisingly, the Homer Simpson ended up being my favorite. Its pretty berry flavored icing and pearlized sprinkles coated the perfectly fluffy donut so that each bite had bursts of intense berry donut flavor. Keep in mind I have a major sweet tooth and the donuts here were on the sweeter side. Bonus, Voodoo is right across from the ‘Keep Portland Weird’ mural, and if you go early, you’ll be able to snag an almost pristine photo. Blue Star keeps things more traditional with a clean decor and while unique, the flavor options are borrowed from something more natural. If I had to compare Blue Star to anything it would be to a craft cocktail bar. You’ll find lemon poppyseed donuts, blueberry rosemary donuts and so on. For either place – go early, you’ll avoid the ridiculously long lines that can build up during popular times.
Supercharge Your Day at Stumptown
Cold brew, varietals and direct trade are all part of what makes Stumptown a mainstay in Portland. The original location in the south eastern part of the city showcases a massive roaster, but with locations throughout the city it’s easy to grab a cup of their liquid lightning.
Expand your Literary Tastes at Powell’s Book Store
Pearl district offers unique shopping experiences, including Powell’s Book Store – the world’s largest used book store. The labyrinth of books takes up a whole city block so if you are a literary buff you could likely spend days in here scavenging around.
Meander the Tea Rose Garden and Japanese Gardens
Visit the Rose City’s eye-poppingly large Tea Rose Garden to enjoy the aromas and colors of these beautiful flowers. Afterward make your way to the Japanese Gardens for
a few moments of solitude among perfectly manicured gardens.
People Watch at the Saturday Market
Don’t be fooled by the name, the Saturday Market runs on both Saturday and Sunday giving you plenty of opportunity to browse the stalls and do some serious people watching.
Imbibe in Portland’s Craft beer Scene
In a perpetual battle with San Diego for the number of micobrews, Portland lands slightly ahead with the most in the country. Which means it’s hard to find a bad beer in this town. Located a little off the beaten path, Hair of the Dog is a craft beer drinker’s ticket to rack up some rare beers for Untappd. Belly up at Dechutes for a flight of lighter beers to rest your feet after walking around the Pearl district. If there is a neighborhood you are interested in checking out, it likely has a brewery.
Eat your Weight Through the City
Be prepared to eat. A lot. Portland’s food scene is on fire and any popular spot is likely worth the wait. Pine State Biscuits will fuel your day with chicken, biscuits and andouille sausage gravy, and the most perfectly golden crunchy hashbrowns I’ve ever had. Devour homemade ice cream at Salt & Straw for an afternoon pick-me-up. The Sea salt & Caramel was my favorite flavour. If you like Mediterranean food then a reservation at Mediterranean Exploration Company is a must. Enjoy their delicately, almost steak-like, grilled Octopus.
Hike to a Waterfall
Portland offers easy access to some of the most beautiful hikes and waterfalls in the Pacific Northwest. Head 30 minutes out of town after grabbing some donuts to the spend an early morning hiking to Multnomah falls. This two-tier, 620 foot beaut is one of Portland’s most popular waterfalls so get here early to avoid the crowds. Continue this hike for the loop and come across a handful of other waterfalls and ditch the crowds. It takes half the day to do the loop, Don’t forget to wear good shoes, layers and a rain jacket!
SPARK YOUR SOUL. SEEK ADVENTURE. GET ON THE LIST.
Subscribe to Headed Anywhere's newsletter to get exclusive advice and inspiration to help spark your soul!