48+ Hours in Portland, Oregon
Updated: May 17
In my quest to visit all 50 states, I realized that I had never been to Oregon—around it, yes, but never in, so we were off on another road trip!
We flew into Portland, Oregon where we rented a car for our two-week adventure. By the time we arrived at the airport, rented a car, and found our hotel, the Sentinel Hotel, we just had time to visit Powell’s City of Books, the largest new and used bookstore in the world, and have dinner at Jake’s Famous Crawfish.
Thankfully, Powell’s was in easy walking distance from the hotel, and it keeps late hours. I have never before been in a bookstore where visitors are provided a map to color-coded areas and workers are on hand to give directions. The multi-story, multi-level building houses surprises around every corner including a rare book section. The café is a great spot to take a break from all the discoveries, but it was still closed due to Covid when we visited. After exploring some of what Powell’s had to offer—and, of course, buying a few hard-to-find books—we walked down the pedestrian street to Jake’s Famous Crawfish. The weather was chilly, so we chose to sit in the clubby-feeling interior and enjoyed a relaxing dinner.
We strolled back to the Sentinel Hotel after dinner and were so glad we were staying there. The staff members were always very friendly and helpful. We asked directions and recommendations multiple times, and someone was always available to provide assistance. The room was small but efficient and was equipped with plenty of mirrors and a coffeemaker! The hotel doesn’t have a restaurant now, but you can order room service from Cheryl’s on Twelfth, a restaurant nearby. We opted to go to Cheryl’s the next morning for breakfast instead and were extremely pleased. Our meal started with a popover that was bits of melt-in-your-mouth goodness. The misshapen bits hid their true lusciousness in a bread that reminded us of beignets.
After the scrumptious breakfast, we hopped in the car and, with info from the hotel staff, headed to the Japanese Garden and the International Rose Test Garden. We were fortunate to find parking along the street between the rose garden and the Japanese Garden. arking is very limited, however, so you may want to consider taking the shuttle during peak tourist season.
The International Rose Test Garden was begun during WWI to ensure that European hybrid roses would survive. The garden has expanded and now contains over 10,000 rose bushes representing more than 600 varieties of roses. The aroma of these hundreds of blooming roses met us before we could even see the colorful blossoms that filled the garden. After strolling around the free garden, we crossed the street to the Portland Japanese Gardens, purchased tickets and walked up the steep, paved pathway to the Cultural Village. The diverse fall colors of the trees, shrubs, and flowers that surround the paths and the many waterways was breathtaking. One of our favorite parts was the Ellie M. Hill Bonsai Terrace where we observed bonsai trees over 400 years old—what a family commitment. Through the use of landscaping, the garden is divided into different area including the Strolling Pond Garden, the Tea Garden, and the Sand and Stone Garden. The peacefulness of the gardens was a good reminder to enjoy all the beauty that nature provides.
Our next stop was at the Pittock Mansion built by Henry and Georgiana Pittock, who are both examples of self-made people. They came to Portland via the arduous Oregon Trail to find a small, backwoods town that they would help develop into the bustling city of Portland as we now know it. Because the house had been updated many times, the preservation group decided to reproduce the house as it was during the period of 1914-1918 when it was first built. The house is small by today’s mansion standards, but the visit was very educational. We were lucky to have a beautiful day, so we made certain to walk to the overlook for a beautiful overview of Portland.
One of our favorite meals of the trip was at Masu Sushi, again within walking distance of our hotel. Masu was originally a square wooden box that was used in Japan to measure rice and is now used to serve sake, a Japanese rice wine. This restaurant used replicas of masu in creative decorations and for serving sake. I won’t bore you with all we ate but the sushi was some of the best we have eaten.
The next morning, we tried to visit the Witch’s Castle. We enjoyed the scenic drive along winding roads, but it did not matter how we approached the castle—and we tried many ways—all roads were closed due to construction. Oh well….perhaps next time.
We had one more stop before we headed back to our hotel—to visit the Freakybuttrue Peculiarium and Museum, a boutique museum featuring what else?!? Things that are hard to believe exist! We enjoyed taking selfies with Krampus and viewing the gruesome dollhouse. Where else can you have your picture taken as you dangle by your fingertips from a skyscraper—and not be scared to death? We even got to play a Theremin—shades of Big, Bang Theory. We had a great time, but I would not recommend it for young children. After our visit to this small, 3 room, quirky museum, we walked through the neighborhood that is full of restaurants, souvenir shops, and liquor stores. We were disappointed that we weren’t hungry because the restaurants, especially Pin State Biscuit Restaurant, came highly recommended by our neighbors.
We parked our car at the hotel and ventured out to explore downtown Portland. By this time we were hungry so it was perfect timing to find a food truck for which Portland is famous. We found a Mediterranean food truck which served excellent gyro, pita, and salad. (Each food truck area seemed to specialize in a particular type of food.)
We located the Lan Su Chinese Gardens, an oasis in the middle of the city. We noticed many differences between the Japanese and Chinese gardens, but both were peaceful. We walked over the many bridges and admired the koi and blooming flowers. The garden was built in collaboration with Portland’s sister city, Suzhou, China. The outside world melted away when we entered the garden and a sense of tranquility immediately descended.
Many people had warned us about the homeless situation in Portland. As we traipsed throughout the city, we did encounter many tents with their owners sitting outside, often in groups. Everyone was polite and friendly, and we had no problem. We took a break for coffee at Stumptown Coffee, another “food” for which Portland is known.
Deschutes Brewery was our dinner for the evening. The hamburger along with a Truffle Ceasar Salad made a perfect combination. Deschutes, the largest craft brewer in Oregon, allows you to make your own beer flight which gives beer connoisseurs, and just plain-old beer drinkers, a great deal of flexibility.
And then our time in Portland was over but our adventure was just beginning. On to Hood River tomorrow!