I had my preconceived ideas about what the city of Portland would be like. I imagined craft coffee, street food everywhere, and yes, a vibe that can only be described as “weird”. I don’t think it’s offensive to call Portland weird, in fact, I think they love it! From funky-hippy bars to crazy colored hair, there will be something surprising you at every turn. Portland is a booming city- in my experience the people are kind, the bars are unique, the food is delicious, and the surrounding area of Oregon is simply breathtaking. So, if you only have a few days to explore this “weird” city, here is what you should do:
Get a Taste of the Well-Known Voodoo Donuts
It’s early, maybe you just got out of the airport or you are making your way out of the hotel room. Head over to the famous Voodoo Donuts and have yourself a taste of a Captain Crunch or Oreo Cream donut. Yes, you might overdose on sugar. Yes, you may get a stomach ache afterward. But hey, the day is young and you are in Portland!
Snap a Picture by the “Keep Portland Weird” Sign
Visiting Voodoo Donuts will place you in a good area downtown where you can walk around and explore shops and restaurants. You can also find the “Keep Portland Weird” sign around here, a fairly iconic “Instagramable” spot.
Explore and Eat at Pine Street Market
Once you are ready for lunch head to Pine Street Market! I love these kinds of markets because they truly give you that ‘big city feel’ with people buzzing around on their lunch breaks or hanging out with friends grabbing a bite to eat. Everything smells and looks amazing and there are a variety of options to choose from. We chose to eat at a Marukin Ramen and Kim Jong Smokehouse (hey, we couldn’t pick just one place), and the food was delicious! What’s neat about Marukin Ramen is that it is a chain ramen restaurant in Japan, and the one in Portland is their first stateside location! On our way out we grabbed hot herbal tea which was perfect to sip on in the cold weather while walking the waterfront.
Visit the Pittock Mansion
For the best view over Portland and to learn some interesting history, head to the Pittock Mansion. You can avoid the entrance fee by walking around the mansion and still be able to enjoy the gardens and the view. The Pittock Mansion was built in 1914, and the informational signs take you through the journey of how Portland transformed from a pioneer town to what it is today.
Hit Happy Hour and Check Out the Bar Scene
Taking a page directly out of the 90’s, the Portland bar scene is weird, unique, and interestingly nostalgic. Known for their beer and live music, Portland’s nightlife is definitely for both those who like to party, and also those who like to relax and enjoy a drink. Some of our favorite spots were:
This fun “dive bar” type of spot is a great first stop to get the night started. The bar dates all the way back to 1902 and has that classic look and feel. In the back, there is a nice lounge area with leather sofas which is the perfect spot to hang out with your friends for a few rounds of drinks.
I’ll get to the full underground experience later on, but the Shanghai Tunnel Bar offers you the perfect taste of the Shanghai Tunnel Experience. You have to take stairs under the city from above ground to reach the bar and the atmosphere is hip, dark and cozy. Their Happy Hour menu also has an awesome selection of drinks and delicious food.
Where ever you go, don’t be afraid to strike up a conversation with the locals. Some of the best recommendations we received were from locals we met who were nice, helpful and truly one of a kind.
Pick a Food Truck, and Try Some Food
One of my favorite parts of exploring a new city is trying out the street food. I live in a city with a fairly non-existent street food scene, so I always get excited at the chance to try some. In Portland, there are plenty of food trucks, food carts, and corner store windows that have excellent foods to chow down on. Portland has even been called “home of the best street food.”
Okay, adrenaline junkies/adventure seekers – this one is for you. Travel underneath the streets of Portland and take a journey back in time to explore the citie’s haunting past. If you are into ghost tours, history, drinking or all the above – you will love this tour! And even if you aren’t, it is pretty astonishing to be able to venture underneath the city and take a look at Portland’s terrible history. The underground tour guides will literally take you below the city where humans were once hidden and smuggled. It’s an interesting way to spend your evening, and you can book a tour for a fairly reasonable price!
Catch a Sport’s Game
Portland has a fantastic sports scene and some awesomely loyal and enthusiastic fans. We were lucky enough to be visiting during the NBA playoffs, and we were able to see the Portland Trail Blazers bring the Moda Stadium to life. Even though they didn’t win – the atmosphere at the game was enough to make the experience worthwhile. Outside the stadium, there was live music, fountains, and singing fans. Inside the stadium, we were treated to a mesmerizing light show and the roar of the crowd is so loud that you can feel it in your chest.
If you aren’t in the area during basketball season, see if there is a soccer game going on. Even though we didn’t catch a game, we were told by some locals that Portland has a huge soccer fan base, and they get pretty rowdy!
The Trail of the Ten Falls is last on my list but my #1 favorite experience in Oregon. I had always heard of the stunning natural beauty of Oregon and had always dreamed of doing a waterfall hike. The Trail of the Ten Falls is a trail in Silver Falls National Park named because of the 10 gorgeous waterfalls along the 8.7-mile loop.
The Trail of the Ten Falls is about a two-hour drive outside of the city of Portland, but it is well worth it. Approaching the South Waterfall my jaw simply dropped. I had never seen such a gorgeous, roaring waterfall before. My favorite part of the experience is that the hike takes you right under the waterfall! The weather was cold and rainy, but because of this weather, we had the unique experience of being the only people in the park. Also, the excess rain caused the waterfall to be rushing and beautifully full. If you love nature and hiking, I can’t recommend this trail enough!
If you are traveling during the rainy season (which is almost year-round in the Pacific Northwest) don’t do what we did and dress underprepared. Be sure to bring a high-quality rain jacket and rain boots. Trust me, you’ll thank me later!