A Portland Walking Tour is one of the best ways to see a city! You can get a feel of what it’s like to live there, and can wander around or talk directly to your guide. You can’t always do that with other types of tours.
Most cities have a lot of different walking tour options, especially if the city is small and/or walkable. Because of the way city planners built Portland, Oregon, it is conducive to great tours! You can walk through most of downtown and see what you like without a car. I did not find a free option in Portland, but I saw that Portland Walking Tours had some good reviews and has been around for a while, so I chose to go with them.
Note: This is NOT a sponsored post. ALL views are mine and not influenced by any discounts or free things from Portland Walking Tours!
Overview of the Best of Portland, Portland Walking Tour
The Portland Walking Tour company offers eight different tours, including one exclusively for chocolate lovers! Each one caters to a different theme. I wanted to learn more about Portland as a city, partly because so many people say it reminds them of Austin, my hometown. I had never been to Portland before, and I am not a foodie. While I would try the food tours on my next trip to Portland, I picked the Best of Portland tour because it focused on introducing Portland as a livable, sustainable city.
I booked the tour online, as it recommends, in the evening the night before. My tour was on a Saturday morning at 10 am, and I booked on Friday night at around 8 pm with no problems. As soon as I booked, I received a welcome email with clarifications for when and where to meet, and where I could park if I wanted to drive.
The meeting place is Pioneer Courthouse Square (701 SW 6th Ave at Yamhill St). The instructions were a bit confusing because there massive construction overhauled the square, obscuring the signs and entrances. However, I finally found it after walking towards the middle of the square, where the door was titled “Portland Walking Tour Here”.
I arrived about 5-10 minutes early, just as the first group was leaving. I waited with my tour guide for the rest of the participants, and it turned out only 3 other people would be on the tour with me!
During the Tour
We started through the area near Pioneer Courthouse, including the Pioneer Courthouse Square and talked about how Portland “works”. In other words, what makes it so different from other similar cities (including public art, neat and small downtown blocks, public transportation). The tour guide was a nice 40-something Portland native, and really clear about how Portland came to be. When talking about the history of the city, he could bring out an iPad and show us old pictures of certain buildings and blocks.
Since Portland’s characteristics really are sustainability and urban design, much of the tour focused on that. The guide pointed out the reasons that public transportation is so much better in Portland than basically any other US city, why you can walk from block to block in a minute or two rather than 5, and why the streets are so straight you can see a mile in each direction on any city corner.
Most of what we saw were art pieces and buildings that have some interesting background, such as the Portland Building on SW 5th Avenue. We went through the art/theater district to the Oregon Historical Society Museum, where we saw the penny that determined the city’s name! We even went inside one of the theaters for a picture and bathroom break. Along the way, the tour guide pointed out several restaurants and bars/breweries that are well-known in Portland as well.
In the end, we passed by Mills End Park and stopped at the Willamette River to talk about bridges, located about 5 minutes south of the Skidmore Fountain. The tour took about 2 hours as predicted, which was perfect for me to go directly to the Portland Saturday Market afterwards!
There was an informal “end” to the tour. We stayed for a couple minutes to ask the tour guide some additional questions and get directions for our next destinations. Other than that, people usually left after giving a cash tip.
[Recommended Read: The Ultimate Portland Bucket List: Oregon, USA]
Overall Verdict on the Portland Walking Tour
The Best of Portland tour was super informative. I am a sucker for learning about a city’s layout, and Portland has a ton of that history to go around! It seemed that at every street corner there was something to point out, and some part of Portland lore that I never knew before. The whole experience was overall very good. I felt like I walked through a huge museum – one that had everything from modern art to history, from city planning to ways to keep a city weird. I could think of worse ways to spend a Saturday morning.
- Detail of the history and stories. As we went to each landmark, we learned a detailed account of Portland’s history. How each part of it got to where it is today was fascinating!
- Small group size. Four people is a pretty tiny group!
- Matching history with the present. It was cool to see the pictures of old Portland, and I would have loved to see even more!
- The route. We saw some key spots in Portland, including the museum block and Portlandia statue. I visited Mills End Park before the tour because I didn’t know we would stop there, but either way it was somewhere I wanted to visit anyway.
- Even the locals were surprised. One couple had lived in PDX for years (the woman was a native) and took the tour because they had a gift certificate. Even they learned something new!
- The route. We didn’t have to walk too far, but I felt we could have covered more ground.
- Views of the public art. Most of them were good. However, at one point we stood on one side of the street looking at a large statue across the street. We should have crossed and seen it up close rather than glance from afar.
- Price. $23 for an adult ticket is okay, but is the edge of pricey. Add on to that the expected 15-20% tip, and that makes a fancy meal. The food, chocolate, underground, and brewery tours are $59 or $79, which is pretty high. I can’t say anything about whether that’s worth it because I haven’t taken those tours, though.
[Recommended Read: The Ultimate Guide to Portland’s Washington Park]
- Lack of “hidden” or “off the beaten track” places. Almost all our stops were surface-level, find-in-a-guidebook type places. Maybe that’s the point of the Best of Portland tour, but then there should be a “Keep Portland Weird tour” option for non-touristy places. Either way, I would have loved to heard about personal places that the guide loves that tourists normally don’t visit.
- No places to sit. While it is a Portland walking tour, it would have been nice to find some ledges along the sidewalk or benches at the parks we stopped at to sit and rest. This was especially because I was wearing a knee brace, which should have signaled to the tour guide that I was recovering from a knee injury.
- The language around tipping. The Portland Walking Tour website and communication emails talk about tips as an expectation. They’re not treated as something you could feel free to do if you enjoyed the tour a lot.
- No maps. For a non-Portland resident, I did not have a great idea of where we were at all times. The guide could have used his iPad to update us on where we were so we could come back later.
- The lack of food and beer recommendations. I want to know where I should grab a bite! A list of recommended places to try would be amazing. After all, it is the Best of Portland I’m looking for!
- No time for pictures! As a travel blogger and traveler in general, I need to and love taking pictures. The only places the guide gave us extra time to take pictures were Portlandia and the Antoinette Hatfield Hall lobby, where we had our bathroom break.
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