Friday, August 21, 2026

Weird, Quirky, Fun Portland


post by Corrine

How bare do I dare? 

I pondered that question as I bicycled from my hotel towards Oregon Park in Portland. Keep Portland Weird is the unofficial cultural slogan of the city and I wanted to experience that vibe. So, I was on my way to the World Naked Bike Ride Portland bike ride.

But could I ride naked in public? I’m not that modest but still. . . 

When I arrived at the park, I chatted with another first-time rider, and we discussed the dilemma of what to do. As we did, more and more people showed up who were in all states of undress. And when surrounded by hundreds of other mostly naked humans, it was easy to disrobe. I ended up riding in just my underwear, and it was such a joyous, fun occasion. A great way to experience the weird, eclectic, whimsical city of Portland.


Portland – Biking, Weirdness, and Biking Weirdness


Since retiring, my daughter Montana and I have made a point of meeting up in new-to-us cities for some mother-daughter bonding and as a chance to explore new places. Last fall we headed to Denver for a few days and this summer we decided to visit Portland. We always try to find weird, fun things to do. That was easy in Portland. I hadn’t ever watched the show Portlandia, so I didn’t really know what a fun and strange place it could be. Lots to choose from!

While researching what to do in Portland, I found out that besides having lots of weird, it also is pretty bike crazy. In fact, Portland actually has two naked bike rides. The first, Portland World Naked Bike Ride, is larger and is mainly a celebration of bikes and bodies. It occurred in July, so I missed it. The one in which I participated, World Naked Bike Ride Portland, is more focused on protest. (It split off from the other one a couple of years ago.) While the second also celebrates bodies of all shapes and sizes, it also serves as a protest for marginalized communities such as LGBTQ+ and immigrants. This year it was also protesting the taking over of our country by billionaires and the closing of the beloved Lloyd Center Mall in Portland. So, besides biking naked, I was also protesting! 


It was while researching things to do in Portland with Montana that I learned the World Naked Bike Ride Portland was happening the weekend prior to our visit. I looked for other biking opportunities, too, and found several. So, I decided to fly down early with my bike.

Biking Portland


One of the biking opportunities I found was the Bridge Pedal Ride. For the past 30 years on the second Sunday of August, Portland has closed all seven bridges across the Willamette River and the surrounding roads (including Interstate 405) to traffic for the Bridge Pedal Ride, a non-competitive celebration of cycling and walking that benefits local health programs. About 10,000 bicyclists participate in this event, following a route that encompasses all the bridges. When I found out it was also happening the weekend I would arrive in Portland, I had to sign up to do it. 


The morning after arriving in Portland, I headed out by bike to pick up my registration material for the Bridge Pedal Ride. I decided to further explore Portland, so I cycled along the riverfront and along the Springwater Corridor bike path. As I was biking along, I realized that I had been on this bike path the previous year when coming through Portland on the first day of my Bike NonStop US bike race. That brought back some fun memories. After reaching the Powell Butte Nature Park and riding some single track, I decided I better turn around as I still had the naked bike ride to do that night. I ended up biking a total of 43 miles that first day.


Portland has one of the best biking infrastructures of any U.S. city I’ve been to. Almost everywhere I biked, I was on either a bike path, a bike route, or a neighborhood greenway. And everywhere I biked, I saw other cyclists. I don’t think I ever went more than five minutes without seeing somebody else on a bike. Portland really is a bike-centric. Between biking and public transportation, I had no need to rent a car.

One of the many beautiful bike paths I cycled on

Early Sunday morning I cycled to the start of the Bridge Pedal Ride meeting more and more cyclists as I got closer. I had breakfast while watching the sun rise on the Fremont Bridge then cycled 23 miles with other bikers for an absolutely fun ride. There was live music on some of the bridges and the views were spectacular. It was fun to see so many families out on bikes. I was finished by 9 AM and since I had the whole afternoon free, I decided to do another bike ride up to Mount Tabor, an extinct volcano within Portland city limits. How weird is that? The area has been turned into a city park and was quite busy on a sunny, Sunday afternoon. By the time I got back to my hotel, I had biked a total of 47 miles for the day.



Live music on the bridge!

Montana wasn’t due to arrive until later Monday, so I had plenty of time Monday morning to bike out and explore some of the trails in Forest Park. This park is within the city limits, yet you feel like you are in the wilderness. So many trails to explore but I had time only for a shorter 27-mile ride before dropping my bike off at our hotel, getting a shower and hopping on the light rail to meet Montana at the airport. It was fun to see so many different areas of Portland by bike and explore some of its city parks. 


Fun With Montana


Montana is not a biker, but Portland has a lot of other things to do. In fact, once Montana arrived, things got even busier. We had made a list of all the fun, weird things we wanted to do in Portland but were limited because Montana was there for less than three days. We certainly tried our best to do as much as we could.

That first night, Montana arrived at 6:30 PM and as soon as we got back downtown, we headed out to catch some live comedy at Al's Den in the basement of McMenamins Crystal Hotel. We got to hear comedians trying out their raw, fresh, unfiltered work. Some of it was good and some of it was pretty bad, but that was part of the fun. Immediately afterward, we walked to the Toasted S’Mores Bar. Who knew such a place existed? Only in weird Portland. Having sweet tooths, we knew we had to experience it. And to our surprise, it just happened to be National S’More Day. How serendipitous! It also meant we got a 25% discount, too! 



The next day was warm and sunny, so we took the train north to the Columbia River to go kayaking. So fun to be out on the water for a few hours. After a late lunch at a Tiki-themed restaurant, we headed back to decide on our evening entertainment. Montana is a singer/songwriter (www.aeyreofficial.com) and wanted to hear live music. I was game for hearing new bands, too. Even on a Tuesday night, there were several options. We finally decided to head to Mississippi Studios to hear three indie rock bands, none of which either of us had ever heard. 

Kayaking on the Columbia River

It was a lot of fun to hear live music and we both agreed that we liked the first band, The Flooks, the best. They performed with paper bags on their heads which was weird yet fun. The venue was full of twenty- and thirty-somethings but nobody seemed to care that an old lady (me) was rocking out, too! By the time we took the bus back to our hotel, it was way past my bedtime!


The 4T Plus 


The next day, I wanted us to do the 4T. This official route includes a Train, a Trail, a Tram, and a Trolley to make a big loop. It sounded like a fun, weird thing that would allow us to see more sights around Portland.

We started by taking the train to Washington Park where we exited 260 feet below ground after going through a three-mile tunnel. (Weird fun fact - this station is the deepest transit station in North America!) You could spend several days exploring Washington Park, a large historic greenspace that features major cultural attractions, but we only had time for a couple of things. 

We take the Train (our first T) to the deepest transit station in North America

We started by visiting the Portland Zoo, which surprised us. It was larger and nicer than we both expected. Both Montana and I have mixed feelings about zoos. We know they are great for advocating for wild animals and educating the public, but we don’t like seeing wild animals fenced in. The animals we were most fascinated by were the weird-looking lamprey eels in the stream and pond section. 


After walking quickly around the zoo to see all the exhibits, we took a shuttle to the International Rose Test Garden. We had no idea that the climate of Portland, with cool, rainy winters and warm summers, was perfect for growing roses. They have a huge garden with over 600 varieties of roses. June is the best month to visit the garden, but there were still plenty of blooms in August. We tried to find the most fragrant roses. It was a beautiful, peaceful place to spend some time, but the 4T trail was calling us.

Just a very small section of the rose garden

Next up was the hike up Marquam Trail. We accessed it from the on ramp to Highway 26 which felt a bit weird. The 4-mile trail climbs to Council Crest at 1076 feet, the highest point in Portland. The section of trail past the high point was closed due to a water main repair, so we had to walk on a steep, busy, winding road with no shoulder instead. Oh well, all part of the adventure. After the high point, the trail drops back down to the Oregon Health and Science University where we accessed the tram

The hiking Trail starts by the on ramp for a busy highway!

After taking the tram back down to the downtown area, we just had a short trolley ride back to our hotel. It was a weird but fun thing to have completed. We were tired but there was no rest for the weary. 

Tram ride back down to downtown Portland

And lastly, our Tram (streetcar) ride back to our hotel

More Exploring and Fun


Next up, we wanted to have dinner at the Hawthorne Asylum Food Carts. Yes, this really was the site of a psychiatric hospital that operated from 1861 to 1883, but it now houses around 20 food carts serving food from Burmese to Greek to Korean Fusion. Another weird Portland oddity but with really good food! Montana had a gyro while I had a Japanese fusion bowl.


And next up for the evening was live improv at the Curious Comedy Theater. We saw online that on Wednesdays the theater welcomes both new and seasoned performers, so we decided to give it a try even though it was outside our comfort zones. Pretty much everybody else at the venue had done improv before, but they welcomed us newbies and it ended up being a lot of fun. It was a totally different group of people than I normally hang out with, but Montana and I really enjoyed participating. We managed to not embarrass ourselves too badly, and even if we had, it wouldn’t have mattered. 


Earlier Montana had noted that there were ghost tours available in downtown Portland. We weren’t sure we could make it in time, but as soon as the improv finished, we rushed out to catch a bus back downtown and made it just in time to buy tickets five minutes before the tour. Whew! The ghost tour wasn’t very scary, but our tour guide was a great storyteller, and we learned quite a bit of history about downtown Portland, including unsolved murders of the past and stories about people seeing and feeling the haunted spirits of those who had died violently and tragically. It was great fun, but I was exhausted by the time we got back to our hotel at 11 PM. We had been going non-stop all day.

There’s Still More


While walking around and exploring Portland we kept seeing these large six-foot painted crows. We found out they are part of an art installation that had been put up the week before we arrived. There are 30 painted crows that all have names and back stories and have been installed in iconic locations all around Portland. They are celebrating an upcoming stop-motion fantasy adventure film based on the novel, Wildwood, that is set in a magical forest around Portland. I downloaded the app and we found a few of the crows on our adventures. 


Finally, Thursday came and it was time for Montana to leave. But my fun wasn’t done. Earlier, I created a biking route that would take me past all the crows. After dropping Montana off at the airport, I went on a quest with my bike to find them all. After 42 miles and 2400 feet of climbing, I had "collected" all the crows.  It was a fun, whimsical adventure to do, and it took me by several well-known Portland landmarks such as the Pittock Mansion, the courthouse, and Voodoo Doughnuts. It was a great way to finish up my time in Portland.

Several of the thirty crow sculptures that I "collected"

I 🩷 Portland


I don’t know if it was the perfect weather (sunny and low 80’s F every day) or the fact that I didn’t have to drive a car in traffic, but I loved Portland. It was quirky and weird and fun. I highly recommend a trip here. I might have to come back. After all, I haven’t experienced the Freakybuttrue Peculiarium or Mill Ends Park, the smallest urban park that consists of just one tree! So many weird and fun things to do. I highly recommend a visit. 

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