🕳️ Dig into the history of the Woodstock Mystery Hole

It’s Wednesday.

And you know what that means … It’s time to get weird.

Every week, we celebrate elements of Portland’s wonderful weirdness in collaboration with Weird Portland United. So far, we have featured The Unipiper, the Portland Sleestak, Spencer Sprocket, Carlos the Rollerblader, Strawberry Pickle, and many more colorful local characters.

Did you miss a story from this series? Don’t worry, you can find our archive of Weird Wednesdays right here.

Today folks, we have a little poem to kick things off:

I dig,

She digs,

He digs,

They dig.

It’s not a long poem, but it’s pretty deep. 

— @Dadsaysjokes on Twitter

Today’s Weird Wednesday requires a miner’s headlamp and a sense of adventure, because we’re talking about the Woodstock Mystery Hole, its history, and the glorious importance of absurdity and fun.

Alrighty, follow us down the Mystery Hole!

Let’s get down to brass tacks — what the heck IS the Woodstock Mystery Hole?

Pun completely intended, but finding that answer took some digging. The first thing you need to know is that the hole (the location of which is not explicitly clear, but we know is two-ish miles off of I-205) is owned and operated by Portlander Barron in the Woodstock neighborhood.

Barron is known for bringing a lot of fun to the table — whether it’s with the Mystery Hole or by hosting meteor-catching parties in his backyard in the summertime.

The Mystery Hole is — simply put — a hole in the ground with an attached ladder that takes you into a couple of subterranean tunnels, where strange wonders can be found.

What follows below is our interview with Barron, edited for length and clarity.

Tell me a little bit about yourself and some of the awesome and weird projects you’ve created?
I’ve been a substitute teacher for over 40 years. It gives me more free time to play than regular teachers’ schedules allow. I’ve enjoyed creating a place where friends can come and have fun.

What exactly is the Mystery Hole?
The “world famous” Woodstock Mystery Hole™ is a mystery, a hole, and it’s in the Woodstock neighborhood. If you knew exactly what it was, it wouldn’t be a mystery.

How did you bring fun to your community during the pandemic?
Like many of us, I took a break from socializing in person except for a very small group. I don’t think I’ve made a lot of fun since March of 2020, but that could change if things go well. I continued substitute teaching online and had the pleasure of teaching fourth grade virtually the last quarter when schools had to provide in-person instruction for those who wanted it.

Right now the Hole is closed to the public, however virtual tours are available on the website and there are a few videos online.

What are some upcoming projects or adventures that are coming up on your end?
Pedalpalooza’s Buck Moon naked bike ride is my next adventure, Friday, July 23. The World Naked Bike Ride was cancelled this year and last, so this will be a smaller version with hundreds instead of thousands of moons.

This Sunday, I’m hosting the first Zombie Croquet Day since 2019, which is always fun. We don’t dress up as zombies. Zombiehood is an attitude not a costume. All players are vaccinated, and we’ll stay about one mallet apart. Anyone can set up a course and the rules, which they’re welcome to the alter, are on my website.

What does keeping Portland weird mean to you?
Keeping our city weird means keeping ourselves weird and accepting weirdness in others — normalizing the abnormal and celebrating neurodivergency. I think we do a fairly good job of it.

How can folks get in touch with you?
My website includes projects and contact information. They could ride to Col Summers Park next Friday evening, but it might be hard to pick me out of the crowd.

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