Once we arrived in Portland, we jumped in an Uber with our driver Tage, which Jon pronounced like “sage” and was quickly corrected. Evidently, you pronounce it, Tah-geee. After a very quiet Uber ride, we safely arrived at our quirky hotel – McMenamins Crystal Hotel. Each room has its own theme inspired by a song or performance from the Crystal Ballroom next door. Ours just so happened to be the room called, “Let’s Call It Love.”
We then headed over to the rooftop at 10 Barrel Brewing just in time for happy hour. The weather was perfect. It was in the 70’s with a slight breeze and the sun was shining bright. I’m not sure what everyone does for a living in Portland, but there were a ton of people already there at 3 pm on a Thursday. I was already loving this city. My only complaint is that they play a lot of alternative rock and zero rap music. But anyways, we had a couple of rounds of their Whitburger pilsner along with some chorizo con queso & honey cajun chicken lollies. We did not try the pizza, but it smelled phenomenal and I have heard good things about it. We decided to walk off some of those calories and head on over to Powell’s City of Books. You could get lost in this bookstore, it is HUGE and there is some adorable set up at every turn like colorful crates and decorated blackboards. Also, this place is fantastic for people watching – Portland gets weird, guys. I dig it.
After grabbing some very strong coffee at the bookstore and attempting to adjust to Pacific time, we went back to the hotel to wash off the travel day and transition to our evening attire (aka jeans.) The plan for the evening was to make sure we got into the Multnomah Whiskey Library. You can make a reservation using their “Hall Pass” program but it is $25 per person. So, we used a pro tip from a friend and put our name in, went to a different restaurant, then headed back over. It was a two hour wait so you have plenty of time to go eat dinner elsewhere and there are tons of restaurants within walking distance, or you can stay in The Green Room downstairs from the Whiskey Library while you wait. They have casual cocktails and light appetizers.
When you walk into the Whiskey Library, you immediately feel like you are part of some elite club. They only let so many people in at one time, hence, the wait. The wall behind the bar is, of course, lined with any whiskey imaginable with rolling ladders up to the top shelf. There are vintage leather couches and chairs and a gorgeous chandelier over the bar area with dim lighting. The bartenders are extremely knowledgeable and each time you order a drink they climb the ladder to bring down the bottle and set it right in front of you after they pour you a glass. I like this concept because you can read the label, take pictures to remember the types you tried, etc. However, I had red wine while Jon enjoyed the whiskey, but nonetheless, I highly recommend this place!
The next morning, we went to Blue Star to try their gourmet donuts, which did not disappoint. They use brioche as their bread base and I wish I could have tried all of them. Next time, I would also like to try Voodoo Doughnut, which has some pretty instagram-worthy donuts.
At this point, we were fueled up on sugary goodness and headed to get a rental car for a day of driving through Oregon’s wine country, Willamette Valley… stay tuned for Part II of the trip – it gets even better!
Recommendations
Hotel
Restaurants & Bars
Doughnuts & Coffee
Things to do
Timeless 