How to Explore Portland, Oregon

For most of the cities and parks on this trip, Stephanie and I have scoured blogs and websites for the best itineraries and points of interest. The first city on our trip, after a ten and a half hour drive the day before (see post here), was Portland!

We had about two days in the City and we wanted to get the most out of it so we stayed pretty organized. I had mapped everything out ahead of time to make sure we were not zig-zagging across the city. When it came down to it, we never felt rushed or like we were missing out.

Here are a couple of ways to staying organized and getting the best out of Portland!

Portland is easy to get around and pretty simple to find parking if you don’t mind putting a few quarters in a meter. The city is organized into 5 areas: North (N), Northeast (NE), Southeast (SE), Southwest (SW) and Northwest (NW), and the streets in each section are named accordingly. You always know where you are!

Start in the West area of the City:

This is the “downtown” district or Portland and has a lot of amazing things to see and experience.

The first place we stopped is Powell’s City of Books. This you will find on every list of things to do in Portland you read, and for good reason, it is incredible! You could get lost trying to explore every nook and cranny of this book store. floor upon floor, shelf upon self filled up to the brim of every kind of book you can imagine, and tons of souvenirs and coffee to boot!

Image by Stephanie Naru

Right across the street from Powell’s City of Books is an “outdoor” shopping strip called Union Way. I put outdoor in quotations because there is a ceiling above your head, but it is strewn with skylights to let the sunshine in. The natural wood finishing and hanging plants made the way very inviting, and the hipstery, lumberjackish apparel shop gave off an exquisite Portland feel.

Of course when in Portland, you must grab coffee, And to get that morning fix while in the SW district, we stopped at Heart Coffee Roasters to pick up two iced coffees with their homemade almond/walnut milk. Heart Coffee Roasters has two different locations, east side and west side, and another one opening soon. Awesome coffee for sure! Caffine fueled, you will be ready to explore!

Next… lunch:

Before the lunch rush. By the time we left the whole block was MOBBED!

Images by Stephanie Naru

Portland is somewhat of a street food phenomenon! Being touted as one of the world’s best street food by CNN, and raved about by Bon appetite, we knew we had to stop at one of Portland’s legendary food pods for lunch. We perused the vendors at the Alder Food Pod (unlike other food trucks, Portland’s street food vendors stay parked in groups around the city making it super convenient to sample a variety and find exactly what you are craving).  we decided on a Wiener Burger from RAD fare (with plenty of innuendos in tail) a vegetarian/vegan burger truck and seriously could not have been more satisfied. Many napkins lost their life that meal.

Image by Stephanie Naru

With bellies full, it is the perfect time to go for a walk! The Williamette River divides the city in half and on the west side there is a lovely little boardwalk where you can gaze at the plethora of bridges that span across the river. There are twelve bridges of all different designs, twelve in all (check out a link here). The Tom McCall Waterfront Park also hosts a number of events and festivals throughout the year, but is also a lovely place to hang out in the shade.

We also got to see this cute little ferry boat on the river. You can catch a glimpse of one of the bridges in the background.
Images by Stephanie Naru

As we walked up the water we came to SW Pine Street. Having done plenty of research and reading I knew I wanted to stop into Pine Street Market. Ceiling laced with string marquee lights, this is another great place to stop in and grab lunch, a drink, or if is something sweet you are after, Portland’s famous Salt and Straw ice cream shop has a location here!

Image by Stephanie Naru

If you are looking for a sunset destination on the West side, we got a recommendation from a local. Pittock Mansion is a French-Renaissance style château sitting in the West Hills of Portland with an incredible view of the city and Mt. Hood on the horizon.

Images by Stephanie Naru

Had the weather been a little less hazy, Mt Hood would have stood out in the distance as she reflected the sun’s setting rays.

West side destinations we didn’t get to see:

Ira Keller Fountain Park (it was unfortunately closed due to maintenance)
Portland Japanese Garden
International Rose Test Garden

Head to the east side for some Portland vibes:

We started on Alberta Street in North East Portland. A cute little street, with another Salt and Straw location, lined with coffee shops and clothing stores. We opted for a vegan ice cream shop called Back to Eden while our devices charged up for more adventure! We drove down Hawthorn street and saw a bunch of retro shops, bars, and theatres.

SE Division Street was probably one of my favorite streets in the South east area of Portland. We hit up some really cool vintage shops, such as Artifact Creative Recycle which will have everything you ever thought or didn’t know you needed, such as green velvet couches, retro sunglasses, and fun sequined tops. The street is also lineed with amazing restaurants! We tried the famous Pok Pok, which was on ever single list I checked out. They serve “the food found in pubs, restaurants, homes, and on the streets of Southeast Asia… specifically from North and Northeast Thailand.” Absolutely incredible and definietly yummy!

Image by Stephanie Naru

After our sunset at Pittock Mansion we headed to Cathedral Park to capture some amazing twilight shots of St. John’s Bridge, the Northern most bridge of the 12. The gothis spires of the bridge along with the soft glow of the street lamps really makes for a gorgeous view. The bridge was incredible sight after the sun was beyond the horizon, but would also be a great destination for sunset.

Image by Stephanie Naru

After a hard day’s exploring we headed to a pub called Wayfinder. Apparently new on the scene, this bar had a lovely outdoor seating area and brewed its own local beer, which is just what we were looking for! Very nice service, and a kick-ass burger and fries to boot! It was the perfect end to our first day in Portland!

Go Outside the City!:

Just outside the cit of Portland is the amazing Multnomah Falls and Oneonta Gorge. Multnomah Falls is one of the most visited recreational sites in the northwest. The drive itself is a thing of beauty and well worth it. The falls features a two drop cascade fed by rainfall and snow melt. There is also a little hike up to Benson Bridge, a footbridge that suspends over the fall’s second drop. Dress warmly and wear good shoes because the spray from the falls makes the area cool and slick.

Image by Stephanie Naru

That being said, Oneonta Gorge is also a place to wear good waterproof shoes! If you do decide to make the trek, you will be walking through quite a bit of water. Again, totally worth it. The moss covered cliff looming up on either side of you as you wade through water and climb over boulders and fallen logs make for quite an adventure.

For Portland natives, hiking is a way of life, so if you are new to town or visiting for a longer period of time definitely get out there and check out the other hikes around the area!

Happy Travels!!!