24-hours in Portland Oregon

Download an interactive guide of this route by clicking here.

good walk oregon chris englert eatwalklearn
I love a good walking city, and Portland, Oregon, proudly owns this moniker as not only a great walking city, but also one where the public transportation is cheap and readily available. On a whim, the Hubs and I jumped on a quick Southwest flight, grabbed a room on Trivago, and arrived in this funky city for a 24-hour, Friday night jaunt to catch Paul McCartney in concert. With three hours to spare before the concert, we decided to foot it to dinner. Here’s how to take a good walk in Portland, Oregon in the beautiful city of Portland.

Portland Bridges

good walk oregon chris englert eatwalklearn

Portland is a city of bridges; I counted at least 9 crossing the Williamette from the east to the west in the downtown area alone. The concert was at the Moda Center, and dinner was across the river in the Pearl Street District. We headed west towards the closest bridge, Steel Bridge. The double-decker, vertical-lift Steel Bridge opened in 1912.

On the bottom level travel were trains, bicycles and pedestrian traffic. The upper level ports the light rail, cars, and more pedestrians. What fun to see all types of modality together in one bridge! Connecting the Rose Quarter and Lloyd District in the east to Old Town Chinatown neighborhood in the west, we took the top level so we could get some great views of the waterway.

Pedestrians Everywhere

good walk oregon chris englert eatwalklearn
It was early afternoon, and pedestrians walked everywhere. We passed cute vintage shops, many architectural firms, odd retailers, and modern offices mixed into this warehouse-style district. The only thing I could concentrate on, though, was aching feet. I had recently changed from my winter shoes to my summer shoes, and my feet weren’t having it. Then like a beacon rising from the depths of foot pain hell, we saw the Keen Garage.

A Garage for Feet

I’m not much to promote the heck out of a store, but Keen nailed it when they put this flagship store in the middle of Portland’s hip Pearl Street District. I’m a bit of a hiking/walking shoe aficionado, and I can recite many models and styles of competing walkers.

Walking, or perhaps with a bit of limping, into the store, my little toe sensors exploded with delight at seeing every model Keen makes nicely displayed in kitschy, garage-style shelving. The Keen salesperson jumped up with questions, I responded with descriptions and Merrell competitive answers, and he rallied back with two new Keen models I’d never tried. $217 later, I walked out of the store with happy feet. Reviews to come!

Happy Hour’s a Thing

Prior to arriving to Portland, I had Facebooked a few friends for dinner recommendations, and I received back a fantastic recommendation for Mediterranean Exposition. It was only 5:00, but we were starved. When we walked in, we found out that Happy Hour was a thing–so much so that Happy Hour seating was sold out. They were seating for dinner though, and our stomachs cried out for us to grab a spot. Within 20 minutes, the house filled. So, note to self. Next time, be sure to secure a reservation.

Drinks with Unpronounceable Flavors

good walk oregon chris englert eatwalklearn

Novo fogo tanager cachac? We don’t drink much, but the drink menu enticed us into trying new things. The drink descriptions made me more curious than confused, and I couldn’t pass up the Maiden Voyage, which was a modern twist on the old-style Manhattan classic. One sip, and I returned it. Way too full of bitters and a blast of eww in my face, I confessed to the waiter I didn’t like it. He recommended the Korazim Collins in return, which I loved. Light, soda-y with a warm whiskey and dash of mint, this drink was memorable and tasty.

No Disappointment Here


As a vegetarian, I’m often under-whelmed by menus, and I’m thrilled when more than one vegetarian option shows up. Here at the Exposition, my taste buds popped up and squealed. Although the menu changes daily according to available ingredients, the waiter ensured me that I would always find a good five options. On this day, I found at least ten.

We started off with the shalosh, 3 flavors of hummus–beet, eggplant, and pumpkin–served with freshly made pita bread. Warm and soft, the bread played palette to the luscious hummus choices, which we polished off in record time. For dinner, I loved the Chreime (being from Denver, I must take advantage of being on the coast and having fresh ocean-caught fish.) Every. Last. Morsel. When the waiter offered up chocolate baklava, I had to decline. I was simply too full.

Full Bellies to Full Brains

good walk oregon chris englert eatwalklearn
We left the Exposition and started heading back toward the concert. A couple of lefts and rights, we stumbled upon my second favorite bookstore in the whole wide world, Powell‘s. I had no idea this bibliophile’s heaven existed, and we couldn’t believe its litmosphere: size, selection, or stacks. I only wished I had more time to get lost in this fabulous find. None the less, Sir Paul was calling, so we promised to return.

Art Everywhere

good walk oregon chris englert eatwalklearn
A good walking city must have good art, and murals graced Portland’s walls. Frankly, I think they could have more. I was pleasantly surprised when we stopped to cross the street and uncovered a street artist selling his file-folder wares. What a treat of a man! He’s been making pins and magnets out of file folders for over 20 years, adding his own unique phrasing to each one. I couldn’t resist one that said, “Congratulations for being a great defensive pedestrian!” and I was more than happy to pony up $5 for this surprise.

We scooted along back toward the river, noticing the pink VooDoo donuts boxes in walkers’ hands. We have a VooDoo in Denver, so I didn’t feel the need to indulge. But if you haven’t had the mysterious sugary love of VooDoo, be sure to stop in.

Another Bridge to Cross

With time getting short, we ambled across the Burnside Bridge. On the National Register of Historic Places, this span took us back across the Williamette and then along the wide and beautiful promenade on the east side of the river. A few folks were enjoying Oregon’s new access to pot as they watched the sun set. We hurried past the moss-covered sidewalk back up to the Rose Center area, just in time to wait in long security lines to see Sir Paul.

Good Walk Oregon

good walk oregon chris englert eatwalklearn
If you’re in Portland for a concert of just a quick getaway, Portland’s a great city to walk. Enjoy a good walk in Portland, Oregon by combining a jaunt across the Williamette and Portland’s wonderful bridge system to really get a flavor for life in Portland. Enjoy, and please post some pics or some feedback!

To get a fully interactive and responsive map for this walk, download it from here.


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handsome hiking couple

Chris and Steve, the empty-nesting nomads, travel the world, one month at a time, housesitting and Airbnbing along the way. We uncover urban walks, great hikes, and vegan/vegetarian eats that other guide books miss. And we throw in a bit about Forex trading along the way.

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