The Best and Worst of Portland with Portland Walking Tours

Portlandia

While I am not a big fan of huge organized tours, I do enjoy a good guided tour every once in a while that teaches me more about a place I am visiting than if I walked around on my own. For our recent trip to Portland, we booked two walking tours with Portland Walking Tours, the Best of Portland Tour and the Underground Portland Tour (or as our guide called it, the worst of Portland).

Best of Portland Tour

The Best of Portland Tour does exactly what it advertises, introduces you to the best of Portland. This does not just include the best sights, but also Portland’s cutting edge environmentally friendly techniques. For instance, the tour starts outside of the Hilton Portland and Executive Tower, which is Green Seal certified and decreases its impact on the environment by doing such things as obtaining its food locally and donating leftover food to a local food bank or sending it to farms for compost. Portland even has trash cans that frequently compact and send out signals when they are ready to be emptied.

The tour is an easy walk of less than a mile and a half. The first stop is Portland’s living room, Pioneer Courthouse Square, a brick stage-like area, which is where you will find the Weather Machine, a mechanic sculpture that predicts the weather every day at noon by playing music, flashing lights, spraying water, and displaying a sun, dragon, or blue heron. Across the street from the square is The Pioneer Courthouse, which opened in 1875 and is the oldest federal building in the Pacific Northwest.

Weather Machine and The Pioneer Courthouse

We then walked down a street with bronze animal statues, including a mother bear with her cubs catching salmon, deer, and otters.

We next headed to the Portland Building, a bright, colorful building designed by Michael Graves. This is where you will also see the symbol of the city, Portlandia, the second largest hammered copper statue in the United States (the first being the Statue of Liberty) created by Raymond Kaskey. Unlike the Statue of Liberty, Portlandia is waxed regularly so it will not turn green, and actually gets darker with time.

Portland Building

The next stop was the Arlene Schnitzer Concert Hall, which opened in 1928. Across the street from the theater are street poles with jesters from different countries.

Arlene Schnitzer Concert Hall

The tour includes many more sites than I have listed, including more parks, buildings, and statues. The tour ended at Mill Ends Park, the world’s smallest park, a mere few hundred square inches.

Mill Ends Park

We joined the morning tour, which ended at lunch time, which was the perfect opportunity to head over to the food trucks.

Underground Portland Tour

The next day we joined the afternoon Underground Portland Tour. The tour meets in front of the Merchant Hotel and Old Town Pizza (also Old Town Brewing Co.). We arrived a bit early and waited for the start of the tour at one of the brewery’s outdoor tables and enjoyed a pint. The tour is also a very easy walk of about a mile.

Portland Underground Tour Meeting Location

You will learn a lot of interesting facts about Portland’s sordid past. The main focus of the tour is Portland’s underground. There are a lot of sensationalized stories about sailors being shanghaied and removed from the city via underground rooms and tunnels. The only thing that is not true is that the tunnels were not used to remove the kidnapped sailors. But sailors were actually kidnapped and put on ships to work and there are a lot of interesting stories about how this would happen, including the cunning machinations of August Erickson, who owned a huge saloon where he would give credit to sailors who had just disembarked from ships and then proceeded to allow them to go beyond their credit within the saloon with drinking, gambling, and women, and then would sell the sailors to sea captains. The sailors would then be shanghaied and put on ships while they were passed out.

Underground tunnels that can be viewed on the Underground Portland Tour

You will also learn about other less than stellar parts of Oregon’s history, such as the atrocious laws applicable to African-Americans, the flooding of Vanport City, the forced 48-hour evacuation of Japantown’s residents to internment camps, and the subsequent turning of Japantown into Chinatown for tourism.

Monument to the 442 Regimental Combat Team which included Japanese Americans who volunteered to serve in World War II while they were being held in American internment camps.

The Underground Portland Tour is a fascinating tour and a lot of fun. Our tour guide Jonah was informative and hilarious and I highly suggest taking a tour with him.

Portland Walking Tours

Portland Walking Tours offers seven different walking tours: Best of Portland, Underground Portland, Beyond Bizarre, Epicurean Excursion, Flavor Street, Chocolate Decadence, and Roses Gone Wild. It is possible to just show up at the meeting spot and join a tour, but if the tour is sold out, you may not be allowed to join. The maximum number of people per tour is 16 to 20 depending on the tour. The smaller groups make for more enjoyable tours. Ticket prices, tour times, and tour durations vary. Our tours were over two hours and tickets were $20 each. However, we booked ahead and paid a discounted price of $18.99 per ticket. A bonus is the Best of Portland tour is dog friendly. Also be aware that other underground tours are sensationalized and give false information.

Henry and Charlie were invited on the walking tour too!

They were not so keen on having their picture taken however.

I used Frommer's Oregon to plan our trip to Oregon.

Have you ever taken a walking tour of Portland, or are there other walking tours you have taken and enjoyed?