Exploring Portland in Two Days (solo)

So, you’ve found yourself in Oregon’s “Rose City”, Portland for 48 hours. What do you do to ensure you see all this beautiful city has to offer? Read this post of course!

In April, I was heading to Portland for a conference and had a solid 48 hours to explore. Never having been before, I wanted to see as much as I could.

My journey would start at none other than Powell’s Book Store, the world’s largest independent bookstore. Covering an entire city block, Powell’s opened in 1971 and has become a Portland landmark. Your trip is not complete without a visit to browse the floor to ceiling shelves of books covering over 68,000 sq. feet. To avoid getting lost:

  • The main entrance is at the corner of 10th and Burnside.
  • Pick up a map at the info desk in the center of the green room, also downloadable here.
  • Restrooms are in the purple room – 2nd level.
  • Cashiers are in the green/orange room which are by the 2 entrances.
  • If you are looking to sell used booked enter at 11th and Couch into the orange room.
  • Each room has information desks with computers to help look up a specific book from their over 1 million in inventory.

For lunch, I crossed the street and stopped into Sizzle Pie where I enjoyed a NYC inspired slice with a Portland twist. Try their homemade sangria too. It hit the spot. What I loved about this place was its intimate and welcoming atmosphere. Perfect for the solo travel woman. At the bar I met two other solo diners who happened to be from NYC – now living in Portland. My connections made would lead me to my evening stop on my first day – Jackknife Bar.

During lunch, I met the GM for Jackknife Bar and being it was a Saturday night and I am a woman in her 30’s who still wants to have fun – I took him up on his offer to swing by his bar to check it out. Located within the Sentinel Hotel, Jackknife offers a candle-lit room, a variety of custom-built seating arrangements, a wraparound bar all surrounding its focal point fireplace. It reminded me a lot of what you would find in the meatpacking district of NYC.

My second day in Portland and last day to venture, would find me exploring natures greatest treasures. I LOVE getting in touch with nature as much as I can. Yes, the city has a lot to offer and I am sure I could have explored more but, the opportunity to get out into the mountains was hard to pass up.

I booked a day trip with Viator that took us to Mt. Hood with a visit along the way to Multnomah Falls, Hood River and the town of Mt. Hood. I was amazed with everything we experienced along the way.

Multnomah Falls was like something straight out of Lord of the Rings. It was lush, colorful, full of sounds from water flowing to birds chirping and just magical. More than 2 million people visit Multnomah Falls each year making it the most visited natural site in the Pacific Northwest. The site has a snack bar, gift shop and full ADA accessible restaurant.

Our next stop was Starvation Creek. Don’t worry, no one starved here. First named Starveout Creek in 1884 after a passenger train got stuck there after a train got stuck in the snow. Blocked by a 20ft snow drift, the passengers spent three weeks shoveling their way out. They got out just in time without depleting all their resources. Very Oregon Trail of them.

Ever want to see prehistoric 10′ long, 500 lb. sturgeon? Make sure to stop at the Bonneville Hatchery – we did. I also got a photo op with an extremely famous Oregon native…Big Foot.


For lunch we made a pit stop in the town of Mt. Hood. I wish I had longer in this cute little town. However, in the hour we had I was able to enjoy a delicious meal and freshly brewed beer at Full Sail Brewery  and stop in a few cute little shops.

Finally at our destination – Timberline Lodge. Did you know you can ski/snowboard here 365 days a year? How awesome is that!

Set high on the shoulder of Mt. Hood, this is one of the most unique high-alpine mountain experiences in North America. Even Hollywood thinks it’s great. Some exterior shots of the lodge were taken to be used in the 1980 film “The Shining”. Fun tip: if you go to the lodges front desk and ask for the ax, you can take photos with it on the main floor.


As a hot cocoa snob, I was very excited to hear that the Timberline Lodge is known for their over the top version. I HAD to try it and I was not disappointed. Cinnamon sticks, caramel crunch, whipped cream and chocolate syrup top the already filling beverage. It is well worth the $10.


On the way home we stopped at a family owned vineyard and fruit stand and took some photos with another member of the cascade mountain range – Mt. Adams. Just another majestic landmark to check off the list.


As my 48 hours of exploration came to an end, I reflected on how lucky I am to have a career that brings me to such beautiful places. My advice to anyone who also has a job that involves travel, make time to explore the cities you are in. You never know when you may be back, and life is too short to let any opportunity to see our beautiful planet pass you by.

Until next time, happy exploring.



Solo Travel Woman

Oh and yes, I did make it to Voodoo donuts. Although they are fun themes and creative flavors – to me they are just another donut. Blue Star is much better.

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