Portland, Oregon can be seen with multiple lenses. When a city’s motto is ‘Keep Portland Weird’ one can’t help but wonder what is in store. We made it our mission to find as many weird gems as possible in our two-day exploration. On the contrary, we found the city to be quite wonderful.
Big cities can be overwhelming. Where to go, where to stay and how to get around are all common concerns. Let me help you take the guesswork out of your trip.
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Transportation in Portland Oregon
We knew ahead of time that we wanted to see Portland’s neighborhoods, surrounding waterfalls and head to the coast for a day. Therefore, we opted to get a rental car. For the most part, metered parking was required both in and around the city. It was typically just over a dollar an hour. If you are going to be in the area for more than a day or two, I recommend downloading the app. It will be quick and efficient from that point on.
Portland is divided into five regions: NW, N, NE, SE, SW. Their addresses are reflective of this and it makes navigation super easy. You get a general idea of where the destination is located just by the navigational abbreviation.
If you don’t want the hassle or the expense of getting a rental car, using Lyft is always a great alternative. Download the app, enter your credit card information and follow the step-by-step instructions. You can use my referral code for Lyft and we’ll both get a sign-up bonus!
Lodging in Portland Oregon
Lodging can be the most expensive part of a trip, but it doesn’t have to be. By planning ahead and becoming a member of Home Exchange, you have the option of staying in a coxy, comfortable home for free.
Our Portland, Oregon Home Exchange was great. We had the entire house to ourselves. It was located next to an arboretum in a semi-secluded neighborhood. It was only a few miles from the Pittock Mansion and Washington Park.
If you would like to become a Home Exchange member, I’d love for you to use my referral code. We both will receive bonus points once you have your home registered. Opening your home to strangers may feel odd at first but the nice thing is they are on the same platform opening their home to strangers as well.
Obviously, staying in a hotel is always an option, too. You can score huge discounts and even free stays by using the Chase credit card. If you don’t have a Chase Ink Business card yet, click here to apply. You’ll get enough bonus points to pay for up to seven nights just by meeting the minimum requirements.
Weird Destination in Portland Oregon
Witch’s Castle at Forest Park
Strange mishaps, a deserted structure and decades of teenagers have created a weird destination that is now visited by thousands of hikers a year. The Witch’s Castle is covered in graffiti and does cast a spooky vibe, even in the daylight hours. For those reasons alone, we knew this was a must see destination.
To access the Witch’s Castle, park near the trailhead at the Balch Gulch Bridge on NW Thurman Street. The large pinecone makes it easy to find. Once you go down the steps, head to your left, going under the bridge. The trail leading to the Witch’s Castle is roughly one mile. You’ll pass by a creek and some massive trees. Overall, the trail is of easy grade and is quite scenic.
Forest Park NW Thurman St. Portland, Oregon
Portland Oregon Is More Wonderful Than Weird
I know the city wants to be known as weird, but I think they do a better job at being wonderful. We were amazed by so many of their destinations versus perplexed. These are a few of our favorites.
The Trees in Portland Oregon
The hike in Forest Park will give you a taste for the abundance of huge trees throughout the city. Other favorites can be found on the trails around the Rose Test Garden.
Kennedy School – lodging, restaurant and bars
If you’re like me, you’ve slept in school before. I wasn’t SUPPOSED to be sleeping in school, but late nights and early mornings don’t mix too well. A propped up book was all I needed for a solid 30 minutes of zzzz’s.
Those hard desks weren’t the best option for rest but a cozy room with a soft bed will work perfectly. The Kennedy School has taken a beautiful elementary school, built in 1914, and converted it into a boutique hotel. Each classroom is divided in two with a private bathroom added to each side. Chalkboards have been left on the walls to create an authentic ambiance. You can slumber and not have to worry about anyone seeing your head nodding off or a bell suddenly waking you up.
This school was very plush for its day. The indoor pool, which would have been used for gym class, is currently the hotel’s spa. The auditorium houses events and performances with wonderful acoustics.
Which bar best matches your personality?
Although this Portland boutique hotel has been open for over two decades, it has added niche bars throughout the premises. Two bars that were closed during our visit include the Detention Bar and the Honors Bar. The bartender gave me a brief overview of each of them and I can’t wait to make a return visit when they are open.
For our visit, we were able to check out the granddaddy, and the newest of the bars: The Boiler Room. Regardless if you grab a drink or not, you will want to take a look around. It can be described as nothing less than a piece of architectural art. The designers took pipes, gauges, vents, and who knows what else that makes up a boiler and created a phenomenal railing and whimsical décor. Unique, mismatched lighting pendants hang from the ceiling. A person can walk around over and over and see something new each time.
Speaking of walking around, you can walk the halls without a hall pass and admire art, notes and memorabilia from when the school was functioning back in the early part of the century. I could go on and on about this place, so you’re going to have to visit it yourself to see why it wowed us to no end.
Kennedy School 5736 NE 33rd Ave. Portland, Oregon 97211
Pittock Mansion – Portland Oregon
As the editor of the Oregonian, Henry Pittock grew the newspaper’s distribution from a weekly periodical to a daily source of news. With that, his bank account grew and a phenomenal, state of the art family home was built. This is a must see when visiting Portland.
To realize that this home was built in 1914 just blows my mind. There were so many advancements incorporated into the home’s building. The architecture and design elements are jaw dropping. The details wow you in every room.
The Pittock Mansion’s den/library is a dream for most any bookworm. Cozy and inviting are only a few of the adjectives that pop into my mind upon seeing the interior of the home. The rooms, along with the tie to the local newspaper, make this a necessity stop for a Portland literary vacation.
Admission to the mansion includes the interior, the grounds and the groundkeeper’s home. It is self-guided but the signs around the home give ample information to give you a well-rounded understanding of the property. This home is part of the Blue Star Museum program, so admission is free with a valid military ID.
Pittock Mansion 3229 NW Pittock Dr. Portland, Oregon
The Sports Bra
A play on words while supporting women sports is what this business is all about. Sports bars can be found all across the world, but they rarely have memorabilia on the walls showcasing professional women and they hardly ever show professional women playing on the big screen. Those notions get flipped on their head at this Portland bar.
The Sports Bra’s walls (even in the bathroom) are covered with women’s jerseys, awards received by women, and murals of women in sports. Big screen tv’s are everywhere and only women’s sports are being shown. It’s quite an empowering vibe. This is a business model I hope to see more of as I travel.
The restaurant offers a full menu of delicious food. We loved the roasted brussel sprouts. If you’re looking for a different side dish, consider a Side of Equity. You can donate $5 to the VOICEINSPORT Foundation to help close the pay gap for women athletes.
Their Happy Hours run from 2pm – 4pm as well as 8pm – 10pm. Discounts are applied to both food and drink items. Open Wed-Sun.
The Sports Bra 212 NE Broadway Portland, Oregon
Portland Oregon Literary Destinations to Enjoy
What does a bookstore, donuts, a mansion, and a neighborhood all have in common? They are the basis for a great literary tour. Creating a trip around literacy is nothing new, yet it is gaining notice by more and more travelers. If you are a bookworm yourself, this might be very intriguing. My Portland Literary Tour lays it all out for you.
Powell’s City of Books
Visiting a bookstore isn’t something new, yet they are becoming fewer and farther between. There’s something totally different about perusing selves upon shelves of possible reads versus clicking online. Supporting an indi bookstore is even better.
Powell’s offers the largest selection of new and used books in the entire world. Floor upon floor is packed with every genre you can imagine. The new and used books are intertwined within the shelves so you only have to look for your topic of interest and go from there.
A fun, pleasant surprise were all of the book themed accessories they had on hand. It’s a perfect shopping opportunity for all of those book lovers on your gift list.
A coffee shop is inside the massive store, but its hours do differ from the store’s hours. There is also a rare book room on the top level and that room also operates on its own hours.
Powell’s City of Books 1005 W. Burnside St. Portland, Oregon
Pearl District
Powell’s is located in the famed Pearl District. This multi-block portion of the city is full of restaurants, art, murals, and shops to visit.
Architecture and Art
A walk around the neighborhood is a great way to admire the historical and new age architecture. Random murals can be seen on various streets.
Portland Food to Savor
Pip’s Original Donuts and Chai
Are you a literary fan of Great Expectations? Yes or no, you’re going to love what Pips Original Donuts and Chai has to offer. Their made to order mini donuts are as tasty as they are adorable. Homemade chai is a perfect complement to these savory bites.
If you happen to visit on your birthday, this generous café will present you with a dozen donuts of your choice. For first timers, I’d recommend two of each variety as they are all scrumptious and so unique.
Pips Original Donuts and Chai 4759 NE Fremont St. Portland, Oregon
The Alphabet District
I have no idea how it got its name, but it’s a fun destination. You will feel like you’ve been transported out of the city and planted in small town USA. This pedestrian friendly district is packed with coffee shops, cafes, boutiques stores, and restaurants.
Thai Bloom!
For a great restaurant choice, head to Thai Bloom for authentic, delicious dishes. Our choices for the evening included mackerel wrapped in banana leaves and a classic dish of Pad Thai. Not one for anything super-hot, I was hesitant when the waitress said my mackerel would be served with a spicey red pepper onion sauce. It was on the side, so I was game. Wow! It became a love-hate relationship. Lol Yes, it did have a bite to it, yet it was SO good.
Thai Bloom! 333 NW 23rd Ave. Portland, Oregon 97210
Smith Teamaker
A flight of tea at Smith Teamaker won’t fill you up, but the warm brews and a few macaroons will at least hold you over. The baristas are very knowledgeable about the tea varieties and can guide you through the ordering process. Each tea comes with a personal card depicting the flavors and the region from which the tea leaves were harvested.
Smith Teamaker (2 locations) 500 23rd St and/or 110 SE Washington St. Portland, Oregon 97210
Supporting Local Entrepreneurs in Portland Oregon
One thing we noticed almost everywhere we went was the great variety of items being sold that had been made or manufactured in Oregon. We first noticed this in the gift shop at the Pittock Mansion and then continued to see it as we made or way around the city. The Alphabet District took this to a whole new level. One store in particular, Tender Loving Empire, was filled to the rim with locally made items of all sorts.
Rose Test Garden
Portland is known as the City of Roses. The Rose Test Garden is a massive display of rows upon rows of roses. Every color, shape, and scent you can imagine will tickle your senses.
The garden is free to enter. Meter parking is available although spaces are limited. Even if you are not a huge rose lover, I’d still allow an hour to walk through the area. We visited the first week of August and there were still plenty of blooms, but we could tell they were past their peak.
Rose Test Garden 400 SW Kingston Ave Portland, Oregon
Portland Oregon’s Holocaust Memorial
As with all Holocaust Memorials, this destination might be small, but its emotional impact is big. The ‘forgotten’ or ‘dropped’ bronze items laying on the pavement as you walk to the memorial wall are grim reminders of those horrific days.
Quotes such as “All of us children were crying for our parents. A guard came over to us and yelled, “Stop all of your whining! See that chimney, see that smoke, smell that stench in the air. There is your parents!” and “The fear has never left me.” are poignant statements posted on the wall.
The memorial is on the right as you approach the Rose Test Garden’s parking lot. Walking from the parking lot to the memorial is a short distance.
Holocaust Memorial 400 SW Kingston Ave. Portland, Oregon
Day Trips from Portland Oregon
You can easily fill several days touring around the city, but you can also take advantage of the proximity to gorgeous waterfalls and a stunning coastline.
The tallest waterfall in the state, Multnomah Falls, is a short 30-minute drive east of Portland. Within an eight-mile stretch along the historic Columbia River Highway, you’ll be able to see four additional impressive falls: Wahkeena, Bridal Veil, Shepperd’s Dell, and Latourell.
I suggest going to Multnomah Falls first and working your way back west as it’s easier to get in and out of the parking lots.
Oregon Coast
Looking to go see the gorgeous Oregonian coast? Roughly one and a half hours west of Portland you’ll come to Haystack Rocks, Cannon Beach, Seaside, and Ecola State Park.
Cannon Beach
Cannon Beach is a cute little artsy beach town. It is full of adorable cottages and mom ‘n pop restaurants. We had breakfast at Pig’N Pancake. Great food and exceptional customer service.
Pig’N Pancake 223 S. Hemlock Cannon Beach, Oregon
There are a multitude of beach access points which makes it very handy as parking can be an issue. The best advice is to arrive early, park in the public parking lot, and walk. Once you get down to the beach, you’ll see the rocks. They are so huge! They are famous for a few different reasons. One, they are geologically cool. Two, puffins and other sea life call them home. And three, Hollywood thinks they’re cool, too. You’ve probably seen them while watching a handful of movies: Kindergarten Cop, Goonies, Free Willy, Twilight, and Point Break.
Tillamook Rock Lighthouse can be seen in the distance. The coastal patrol had telescopes set up on the beach by their truck during our visit. This allowed us to see the lighthouse as well as puffins and other shorebirds.
Ecola State Park
We saw a moose at Ecola State Park! We were so excited. He was busy chomping away at the grass and didn’t pay us any attention, but he sure had ours. Besides trying to spot a moose, the next best thing to do at Ecola State Park is to hike to Crescent Beach. It’s gorgeous! The hike has elevation, roots and massive trees. That being said, I recommend close toed shoes. More haystack rocks can be found along this beach as well, but they are not as big as the ones at Cannon Beach.
Seaside
To be honest, we weren’t that impressed with Seaside. It has a few cool buildings and the significant Lewis and Clark statute, but, overall, it was pretty touristy. If you’re looking for souvenirs, it fits the bill.
Portland and its surrounding areas made for a very well-rounded vacation. Nature at its finest. Food that was well prepared and delicious. History and restoration in high style. Innovation and support were flying proudly everywhere we went. Small town charm within a big city. Weird? Sometimes. Wonderful? Most definitely!
