Otaru's Dying Fairs

Yesterday morning, after a nice cup of coffee and a walk, we came upon a street fair.

I grew up at street fairs. My parents sold bedding… sheets, pillows, comforters… at fairs all across New York. Brighton Beach. 9th Street in Manhattan. Nassau Coliseum.

It was big business. In the 90s my dad ran three booths at a single fair — selling the same stuff at each end and one in the middle. People shoulder to shoulder for blocks… the biggest city in the world pouring out to shop, eat, play games.

If you Google old photos of these fairs, they’re incredible. And they hit you with a strange kind of sadness… a longing for a time that’s just gone. The world we live in now is so much more isolated, and street fairs are just one small example of how much we’ve lost.

So anytime I see one, I have to stop and walk through it.

And this street fair is dying the same death as the ones back home… just for a completely different reason.

My cousin gave the street fair business a shot in the mid-2010s, using my dad’s old bedding connect. There was still a little life in it then (it’s even worse now), but not enough to make a killing the way my parents did. My dad once did $60K in sales in a single weekend in the 90s. That was an unbelievable living back then.

Then online shopping exploded, the pandemic hit, and that was basically the end of it for sellers. Food still does fine… people will always come out for a food fair. But household goods? Clothes? Nobody’s buying that off a folding table anymore. They order it on Amazon and have it by tomorrow.

But Otaru’s fair isn’t dying because of Amazon.

It’s dying because there’s almost no people left.

We met a young kid named Ryo running a booth, giving away toys and gifts if you could land a ring toss on an antler horn. We got to talking for a while. His dad was born here in Otaru, and he told us that when he was growing up this fair was packed… booths and bodies shoulder to shoulder all the way down the street.

The fair we were standing in was half that size. And we counted maybe thirty people walking the fair.

Thirty.

A little further down, we met an old man with a row of games that had to be forty years old. 100 yen to play… about 62 cents. They looked like he’d built every one of them himself, by hand, a long time ago. His booth was empty. So of course we played,.

We hit him with a couple rehearsed jokes we say to basically everyone.

I point to myself and say “shachō” which means boss, and then I point to Nick and say “Kouhai” which means like Junior or underling.

We all laughed.

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You walk through a place like this and your brain fills in everything that’s missing… the noise, the crowds, the kids, the haggling… and what’s actually in front of you is so quiet. Not because the fair is bad. Because you can feel exactly what it used to be and you can feel that it’s not coming back on its own.

That’s the part people don’t get about rural Japan. It isn’t that these towns failed. The shops are still beautiful. The games still work. The old man is still there, setting up. There’s just no one left to show up for him.

Ryo told us he welcomes foreigners coming here and buying houses… as long as they come with respect for the culture and the people.

And honestly, that conversation only made me more certain that what we’re doing is a good thing for a town like Otaru.

It needs people. Spending money. Walking the streets. Keeping the shops and the fairs and the old men with handmade games alive.

And yeah… a lot of people buy here planning to come for a week in the winter and not much more.

But look at me.

I started exactly the same way. And now I’m standing in Otaru writing this article, building businesses here, employing local people.

So I have no doubt more people like me are coming. More people are going to fall for this town the way I did… and start showing up, and spending, and investing in places like Otaru.

Maybe one day a kid like Ryo gets to run his booth in packed crowd again.

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This content is for informational and educational purposes only and reflects my personal opinions and experience. I am not a licensed financial advisor, tax advisor, or attorney. Readers should conduct their own due diligence and consult qualified professionals before making any investment decisions.