Anything but Boring around Portland!


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Portland, OR → Boring, OR → Portland, OR
71.1 mi (114.4 km)

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Hitch up your wagons, everyone!

This morning, I woke up bright and early in the city of Portland for some weird and wild adventures through history and local lore! It was the kind of cloudy day you’d expect in the Pacific Northwest, which was just fine for this fur-covered adventurer as I headed south to Oregon City, where the famed Oregon Trail reached its end!

Originally set up by fur traders between 1811 and 1840, the Oregon Trail stretched 2,170 miles from the Missouri River to what was then British Oregon Territory. From the first wagons in 1839 to the Trail’s decline in the late 1850s, over 268,000 emigrants traveled this path to farm the valleys of the Willamette!

It was slow going, though, about four to five months to reach Oregon by wagon, and full of peril! Folks had to contend with diseases (like DYSENTERY!), poor nutrition (scurvy, anyone?), attacks from the different tribes whose land they were plowing through, and even getting run over by the wagons themselves! Apart from the long, hot Plains, they had to cross both the Rocky Mountains and the Dalles. When, and if, they did arrive in Oregon, they then had to content with being in British Territory!

Chief Factor of Fort Vancouver, John McLoughlin, wasn’t the sort to turn folks away after they’d traveled all that distance, so he directed new arrivals south from what is now Portland to Oregon City. This was to redirect American influence south of British territory, add folks to the city that Mr. McLoughlin himself had invested in, and add commerce to the store that the Hudson’s Bay Company was running in that city. By 1844, if anyone wanted to file a land claim in Oregon Territory, they had to register in Oregon City first!

Mr. McLoughlin’s charity was much larger than his profit, though, and by the end of his life, he had extended thousands of dollars in credit to pioneer families that never got repaid. Today, his retirement home in Oregon City is a National Historic Site!

While Oregon City was the first capital after the US took over Oregon Territory in 1849, by 1853, that title had moved to Salem, and the newly built Panama Railroad made ocean transport more efficient than overland. That led to the rise of a port city on the Willamette and Columbia Rivers, named in a coin toss between Francis Pettigrove and Asa Lovejoy. This, of course, was the city of Portland, now represented by a famous, trident-wielding statue called Portlandia!

The saying “Keep Portland Weird” definitely applied to my visit and not necessarily in a fun way. As I visited the Nationally Registered Multnomah County Courthouse and Portland City Hall, I couldn’t help but notice the boarded up windows that were so familiar from my own neighborhood back in LA, even as high up as the sixth floor! I figured it would have something to do with the summer’s unrest.

Sure enough, the broken windows were the result of the historically huge protests against the killing of George Floyd back in May! Portland’s protests were unique, though. Federal troops from a cocktail of departments assembled here to protect the government buildings from damage under Executive Order 13933, and during the chaos that followed, they tear-gassed the mayor, pulled protestors into unmarked vans, and beat, gassed, and pepper-sprayed protestors so much that the very first “Wall of Moms” assembled here, putting their bodies between protestors and federal agents! They also got tear-gassed.

The last major protest had wrapped about a month ago by the time I was walking around downtown Portland, but graffiti still loomed large on the buildings, and Courthouse Square was still full of tents. But, like in LA, art was also starting to cover the graffiti, which is always a hopeful sign that Portland will rebuild better than before, and by better, I mean less abusive toward Black folks and the non-Black folks who care about them!

I didn’t give myself a lot of time in the City of Roses, but I did need to visit something a little lighter before my flight back to LA. Mill Ends Park was just the ticket. At two feet in diameter, it’s the world’s smallest park! With the help of journalist, Dick Fagan, who wrote a column called Mill Ends in the Oregon Journal, what was once meant for a light pole became a park on St. Patrick’s Day 1948! It’s also been hailed as the only leprechaun colony west of Ireland, but on my visit, I did not see a single leprechaun, only a small oak tree!

As if to say all this morning’s activity wasn’t interesting enough, my next destination was the city of Boring! It was not the name I expected for the hometown of the North American Bigfoot Center (actually named for Union veteran, William Harrison Boring)! Only open since last year, this is Oregon’s center for Bigfoot knowledge, founded by Cliff Barackman from the show Finding Bigfoot! I hadn’t been in a Bigfoot museum for quite a while, and I was curious how this one compared to California’s!

Clackamas County is Oregon’s biggest hotspot of Bigfoot sightings, probably because it includes a huge swathe of forest leading up to the west side of Mount Hood! It would be an imposing sight to stumble across a Sasquatch in person, which was very clear from the huge replica named Murphy greeting folks at the entrance of the exhibit! And it sure was a greeting, with the museum’s soundtrack of hoots and knocks playing overhead!

It was a big building but a small museum with two rooms of displays. It covered all the bases of Bigfoot, with foot casts and anatomical diagrams to native depictions of the hairy critter around the world, but something about it left me a little underwhelmed. Even though it was a lot bigger than the Bigfoot Discovery Center in Felton, it felt a lot more generic, sort of an intro to Bigfoot. It touched on local sightings, but didn’t give the in-depth local perspective that gave California’s two Bigfoot museums such charm. I think it has room to grow, and who knows? It may be the place that gives us proof of Bigfoot’s existence! Keep scanning the woods!

Hardly a boring trip by any means, this exploration of northwest Oregon had to come to an end nonetheless. On the plane ride home, I wondered what the future of travel was going to be with the COVID-19 pandemic still raging, with possibilities of more unrest to look forward to. It’ll be important to roll with the punches like rolling on a log, so if I don’t see you until next year…

Keep adventure in your heart!



Previous Day
Total Ground Covered:
804.1 mi (1,294.0 km)

More 2020 Adventures

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