Weird Things to Do in Portland - Travel for Your Life

Weird Things to Do in Portland

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Portland is undoubtedly one of the coolest places you could visit on the West Coast. From spooky museums to eccentric events in downtown Portland, the city is famous for cool and unusual things. The locals have accepted the “Keep Portland Weird” motto because it makes their hometown stand out.

If you are planning to travel to Portland, there is no shortage of fun things to do here.

The city itself has a unique vibe that will make you feel like you are a part of the community right away. Craft beer is all the rage here, and you’ll get a chance to taste rare specialties such as bone marrow flavored ice cream. We’ve put together a list of must-see attractions in Portland but of the unusual kind. It could come in handy if you plan on exploring the weird side of Portland. So let’s dive in!


5 Weird Things to Do in Portland, Oregon

Shanghai Tunnels | The Freakybuttrue Peculiarium | Mill Ends Park | World Naked Bike Ride | Kennedy School


1. Shanghai Tunnels


Shanghai Tunnels

Source: Ben Walton Flickr

There are many myths and legends about the Shanghai Tunnels. The immense network of underground passages underneath the Old Town Chinatown is both mysterious and scary. The tales say that the tunnels stretched to the shores of Columbia River, making it easy to smuggle various goods that came into the port. Of course, there is also a dark side to the lore that includes slavery, prostitution, and murder. The tunnels were connected to rooms that served as brothels and opium dens.

The lack of documentation makes it difficult to confirm these stories today. Not to mention that a large portion of the passages are not accessible. However, you can still go on a walking tour of the Shanghai Tunnels.

Keep in mind that the tour is short since the tunnels are collapsed, but you will hear a lot of fascinating facts about this place and the history that surrounds it.


2. The Freakybuttrue Peculiarium


weird things to see in portland

Source: WikiCommons

Even though it might look like a Halloween Store, the Freakybuttrue Peculiarium is essentially a museum, celebrating all things weird and gory. A local adventurer Conrad Talmadge Elwood came up with the idea for this unique salon in his sleep. Elwood made his dreams come true when he established the Freakybuttrue Peculiarium back in 1967.

Considering that he was a passionate traveler, always on the lookout for weird things, Elwood curated an incredible collection of oddities from all around the globe.

The museum expanded over the decades and now features interactive exhibits that allow visitors to learn more about the Big Foot, alien abductions, and scary urban legends. Ghost hunters can see the haunted dollhouse and other peculiar items that will make your hair stand on end. The museum’s shop is the perfect place to acquire strange books, comic books, scary candy shaped like insects, and other curiosities.


3. Mill Ends Park


Mill Ends Park

Source: Craig Dietrich

Did you know that Portland is the home of the world’s smallest park? Mill Ends Park entered the Guinness Book of World Records in 1971. The park is only two feet wide, so many locals pass right by it every single day without realizing it is even there. The man who started this tiny park is Dick Fagan, a journalist who worked nearby. He saw a hole (intended for a light pole) from his office window and noticed that the weeds started to grow there.

Fagan started planting flowers in the hole, creating his little garden surrounded by concrete. He created a magical journal that included leprechauns and covered it extensively in his Oregon Journal column. Fagan passed away in 1969, but the small park still stands on the Naito Parkway.

Mill Ends Park is an important part of Portland’s lore and a mandatory stop during the St. Patrick’s Day celebration.


4. World Naked Bike Ride


Portland Naked Bike Ride

Source: WikiCommons

The residents of Portland love their bikes and are environmentally friendly. It therefore comes as no surprise that they are a part of the World Naked Bike Ride, a global protest against the dependency on oil. Portlanders have been hitting the streets naked on their bikes since June 2004, and today they have the biggest World Naked Bike Ride drawing in thousands of people every year.

This event has an air of mystery, as the route is kept a secret, and it changes annually. The participants are informed about the ride’s starting point, and that’s it. The streets of Portland are closed off by the police, allowing bikers to enjoy the ride without thinking about the traffic.

The World Naked Bike Ride is a very festive event, encouraging the participants to make it as fun and creative as possible. The bikers wear costumes, colorful socks, decorated helmets, and masks if they are feeling shy.


5. Kennedy School


Kennedy School Hotel

Source: Webvisions 2010 (cc) Shashi Bellamkonda Social Media Swami Network Solutions Flickr.

If you are looking for an unusual place to stay during your visit to Portland, look no further than the Kennedy School. This former elementary school was built in 1915 but was abandoned in the 1970s.

The beautiful architecture and historical importance were enough to attract a large hotel chain from Portland. They renovated the building in the 1990s and kept many cool details. The classrooms were turned into the guest rooms, with old chalkboards as decorations.

Wall art is simply one of a kind in this unusual hotel. Visitors can see old school photos hanging in the halls, as well as murals celebrating the former teachers. Torn workbook pages decorate the walls. The former cafeteria is a restaurant serving local delicacies, while the detention room became a small bar.

Guests who want to party all night long could head out to the boiler room that features a jukebox and a pool table.



Final thoughts

While Portland is known around the world for coffee culture and craft beer, you will find plenty of weird things to do and see around the city. This list covers the most visited locations, but we encourage you to explore the place for yourself too.

You could discover even more unusual locations, such as the vegan strip club, or the hangar at the Oaks Amusement Park that hosts explosive roller derby bouts. If you are into quirky and unconventional events, pack your bags and go on a road trip because Oregon’s largest city is the place for you.


What’s your favorite weird thing to do in Portland? Let me know in the comments below.

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I quit my job to travel in 2014 and it's one of the best decisions I've ever made. I know first hand how hard it can be to get everything in place in order to be able to travel, to know what to pack and where to go, let alone how best to go about your travels once on the road. Here I share everything I've learnt so far so you don't have to learn through as much "trial and error" as I did...Read more

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