**This post was updated January 16, 2024**

Walking in Portland makes for a fine way to spend an afternoon. Many of its main attractions are within walking distance, not to mention a plethora of restaurants, food carts, and coffee houses along the way. It is a fantastic dive deep into this city – to find its history, its surprises, and its quirkiness. 

**Disclaimer: This post contains affiliate links. When you click through a book a tour, I receive a small commission at no extra cost to you. 

Rather have a guided walking tour of Portland?

I highly recommend booking this professionally-guided walking tour of downtown Portland. It’s a delightful 1.5-mile stroll through Portland’s rich history and vibrant culture! You’ll get to explore iconic historical sites, lively public squares, and some truly creative city planning concepts, all while having a chuckle at some funny trivia.

But if you are more of an independent explorer, read on!

Join me on a walking tour of Portland, OR with these self-guiding walking tours. I hope this will entice you to come to visit at some point in your future and discover your next favorite Portland haunt!

Walking Tour Portland – Downtown Park Blocks

Start at my alma mater, Portland State University, at 18th and SW Broadway. It is a gorgeous campus that holds a farmers market every Saturday. Check them out here for hours of operation. But if you’re coming on a day that’s not Saturday, the campus is still a gorgeous place to explore. It’s so green! There are gardens, LOTS of trees, and park benches to sit and just take it all in.

Be sure to visit the PSU Library; a huge, 4-story library that is open to the public.

A few blocks east is the Portland Art Museum, one of the oldest art museums in the country. Directly across the street is the Oregon Historical Society Museum. A block further down is another classic Portland institution, the Arlene Schnitzer Concert Hall. Over the years, I have seen the likes of Hugh Laurie play with his band, the astrophysicist Neil DeGrasse Tyson, and the actor/comedian Eddie Izzard, all perform or give talks here.

Here you will come to the end of the park. Take a right on Salmon Street, and you will run into the historic Heathman Hotel. If you want to splurge for a night, stay here, as they have uniquely decorated rooms. Then continue down two more blocks. You are now in “Portland’s Living Room,” Pioneer Square.

Look up! All around you, there are multi-storied and historical buildings that form quite the cityscape in the heart of downtown Portland. Each of these buildings has interesting architecture and each has its own story to tell.

This is a great place to people watch. There are a few food carts here if you’re hungry, along with a smattering of outdoor tables. There is also a Starbucks in the Square. So indulge and take a load off your feet for a bit. Look for the post with many signs pointing in different directions to destinations worldwide. Also, look for the “Portland Man” statue – he’s holding an umbrella and running towards something. But what?

Across the street to the south is Portland City Hall. Here you can take a self-guided tour (on select days and times) but just the outside of the building is pretty impressive in itself.

The Pearl District

For starters, this is a great place to get your brew and art on! Start with a beer or cider at any one (or more) of the pubs along the “Brewery Block” which consists of such historical buildings as the Portland Armory and Blitz-Weinhard Brewery building. Then head over the world’s largest independent bookstore, Powell’s Books. Within these walls, there are over 1 million books (yes, I said that right) and you can pick up a color-coded map at the entrance to find your way around. In case you’re wondering, yes, there’s a café inside if you need to take a break from your book adventure.

A few blocks east and down the hill a bit is Chinatown. While this one certainly does not hold a candle to San Francisco’s or Vancouver, B.C.’s Chinatown, it is definitely worth at least looking at the ornately decorated entrance. And they do have a couple of really good Chinese restaurants here, as well as the Chinese Gardens.

Not far from here is a cluster of art galleries, such as Elisabeth Jones Art Center, Upfor Gallery, Nine2Five Gallery, and the Art Institute of Portland. Here is a great website with other art galleries in this area.

The Pearl is great for shopping, whether that is a national chain or small boutique. Just walk along Couch St (pronounced “cooch”) from 10^th to about 14^th avenues and you will run into some great shops and restaurants. Also, 13^th and Everett has some great boutique shops, and for lunch or dinner.

To round out your walk (or start it, it’s your choice) go to The Fields Park, on NW 10^th and Overton. This is a small urban park, but it’s unique in all of the natural grasses and flowers you’ll find here. There are benches to sit on and lovely ponds to gaze in.

Belmont and Hawthorne Streets

For a more bohemian walking tour (and let’s face it, so much about Portland is bohemian) head to the east side and explore the parallel streets of Belmont and Hawthorne. You can start on one or the other, as they are a mere six blocks from each other.

As in a previous blog post, much of the charm of Hawthorne has been lost with gentrification, but the shining pearls of this great street remain!

McMenamins Baghdad Theater is worth a visit. This historic building hosts first-run movies and of course, a tasty brewpub right next door. The beauty of a McMenamin’s theater is that they have beer, wine, pizza, and other tasty nibbles in addition to your (also very tasty) popcorn, which you can enjoy during the movie.

Further down the street at Hawthorne and 39^th is one of Portland’s oldest venues, the Hawthorne Theatre. And right next door is a comedy club! 

When you get hungry and need one of the best pies in Portland, walk up to Apizza Schools on 47^th and Hawthorne. Call ahead to be sure you get your pie by the time you get there, so you don’t have to wait. They make every delectable pizza hot and fresh. Pro tip: better make that lunch, because they only make a certain amount of house-made dough every day, and when it’s gone, it’s GONE.

On your way north up to Belmont Street, be sure to meander a little bit in the residential areas. Some of Portland’s most wonderfully “Portlandic” houses are in this neighborhood, and you will get a true feel for some of the classic old Portland homes to be found throughout the city.

Now that you’ve reached Belmont, take a break at the Horse Brass Pub. This British-themed pub offers a ton of foreign brews, with down-home traditional dishes from the U.K. Scotch Eggs, or Bangers and Mash, anyone?

Walk up and down this historic street from 28^th to 39^th avenues – you will run into loads of unique shops and restaurants.

THEN…finish out your day at Laurelhurst Park, just five blocks north of Belmont on 39^th and SE Stark. (39^th St is also called Caesar E. Chavez Blvd.) It’s a huge gorgeous park with walking trails, places to picnic and a large duck pond.

There are so many nooks and crannies in Portland to explore and discover. Dare to get off the beaten path and find your own Rose City oasis!