Blog Post

Photo credits: Piers van der Merwe

One of the best ways to get to know a city is to just walk around and explore. Downtown Portland, Oregon is small enough for you to be able to cover a lot of it on foot in one day.

If you decide to “walk” the city, there are 3 ways you can do this. You can book a tour run by a tour guide. Portland Walking Tours has great reviews and currently costs $21.99 per adult (less for children). There are different tours to select and you obviously have a knowledgeable person showing you around and sharing interesting facts about the city.

If you prefer to go it alone and move at your own pace, I would suggest you find places of interest and drop pins on a google map. Then plan a walking route based on the location of your pins.

The third way is to purchase a Stray Boots Scavenger Hunt. This is what we did on our recent trip to Portland. You play on your phone, in your own time, solving clues as you walk around the city.Once you get an answer correct you will be provided with extra info and photos ie it becomes a self-guided tour of the city!! In addition, you have to take photos as part of the hunt so  you end up with a nice digital record of some of what you have seen. You can often find great offers on Groupon for them, so do check before you buy.

Stray Boots Hunts are not timed so you can stop along the way to spend more time at any of the places that interest you. We typically stop for some refreshment mid-way as each hunt takes about 2 hours. For more info on Stray Boots hunts, you can read this post.

We completed 2 of the Portland Stray Boots Scavenger Hunts and these are some of the places you want to be sure to see if you decide to create your own walking tour or just want to visit a few places:

Powell’s Books – this is a HUGE used book store. It is very well laid out and unless you completely hate books, you need to spend at least a few minutes there. Read our detailed post to learn more about it.

Deschutes Pub – Just across the road from Powell’s is a great place to eat and have a beer. We stopped here for lunch and can highly recommend it.

Portland Art Museum – Our hunt had us viewing the really interesting sculptures outside the building, but we returned later to see inside too. Usually, admission is $19.99 for adults (discounted for seniors and students and free to under 17 year olds) but if happen to be there on the first Thursday of a month as we were, you can get in free from 5-8 pm. The museum has a number of  works by very well-known European artists like Monet and Gauguin and Degas, but also American art, photography and modern art. We spent an enjoyable hour wandering around.

Portlandia Statue – You may never have heard of this statue, even though it is the second largest hammered-copper statue in the US after the Statue of Liberty. That’s because the artist, Raymond Kaskey, holds the copyright for the image and has threatened to sue anyone using it for commercial purposes. So make sure to see it while you are there. You can find it at 1120 SW 5th Avenue on top of the Portland Building.

South Park Blocks  – 12 blocks of park stretch across downtown Portland. Here you will find sculptures, fountains, a peace memorial and a playground. On Wednesdays and Saturdays there are also bustling farmer’s markets that add to the appeal.

Oregon Historical Society Museum – In the lobby, you will find the Portland Penny – the coin that determined the name of the city. Stop by to see that and read the story behind it. We did not go into the museum but the Tripadvisor reviews indicate that it is an interesting small museum that has a large section devoted to the Oregon Trail.

Multnomah County Central Library – Yes, I am recommending you stop by a library! This one is housed in a beautiful old building and inside there is a sweeping staircase up to the higher levels. And you can also see Beverly Cleary “stuck” in a wall outside the children’s room.

Director Park – If you need a break on your walk, this park is perfect to rest in. There are ample tables and chairs available, there are fountains for kids to play in and a giant chess set you can either play with – or watch a game in progress. There is even a restaurant in the park or you could pick up something to eat from nearby food trucks.

Tom McCall Waterfront Park – take a walk along the paths and watch the boats on the Willamette River. Look out for the Battleship Oregon Memorial.

If you have any other suggestions of places one should visit on a walking tour of Portland, please share with us in the comments.