Swinging in the Street: Winona, Minnesota

Swinging in the Street: Winona, Minnesota’s Annual Dance Party

Take a step back in time at Swinging in the Street – Winona, Minnesota’s annual dance party. This event celebrates community and brings together all ages for some good, old-fashioned fun.

Hi guys, Jack here from Travel with Jack and Kitty. We had a fun weekend. On Friday, Kitty and went to Swinging in the Street: Winona, Minnesota‘s dance party. We thought it’d be fun to show you what it was like. So we made a little video…it also inspired me to write this short travel essay.

Setting sun in downtown Winona, MN as the Swinging in the Street event sees dancers on the streets.

Swinging in the Street in Winona, Minnesota

Something I Was Searching For

I was always a weird, weird kid.

When I was about five or six I was rummaging through the attic and found a stack of these weird looking things. I found out they were called records. But they weren’t normal records like you find Taylor Swift selling at Target. No, these were called 78s. What that means is that when you put them on a turntable they spin really, really fast. 78 revolutions per minute. Taylor Swift spins her music at 33 and 1/3 revolutions a minute.

These 78s, well, they were from a way long time ago. In fact, they were around for the birth of recorded sound.

Without realizing it, up in the attic I had found my great grandpa’s record collection. Old hot jazz, big band swing and old-timey polka’s. This was the music he listened to when he was a kid. And now, I was a kid, listening to the same thing.

A big band plays swing jazz at Swinging in the Street in downtown Winona Minnesota

Those 78 revolutions per minute ended up stirring a revolution in the way I saw the world. I stopped watching what was on TV and started looking for old movies. Scenes from a black and white world were things were simple, time was slow and folks were kind. Not like the world I found myself living in.

The vintage records, the old films, the culture I was becoming obsessed with – it set the stage for something I would spend my adolescence and early adulthood searching for: a home that was simple, were time moved slow and folks were kind.

Street dancers at the Swinging in the Street event in downtown Winona Minnesota

The Search Brought Me Around the World

That search brought me around the world. Kitty and I have lived everywhere from Nashville to New York, Burlington, Vermont to Tulsa, Oklahoma. With a lot of stops in between.

For some reason, the town of Winona was always in the back of mind. Like an old movie flickering in and out of the shadows of time, or like an old record that keeps on playing…the sounds in the grooves never fading away.


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You see, I went to school here. Flunked by way out of a creative writing degree at Winona State University. Somehow I’ve made my living as a writer. I guess life is funny that way. I didn’t really like going to college here, in fact, I hated it. But what I did like was the town. The feel. The vibe. I grew up in Minneapolis and no matter how many times Kitty and I tried living in the Twin Cities we’d always wanna escape to Winona whenever we’d have a free weekend.

Somehow we found ourselves back in Winona. Moved back here late, last summer. There was no grand plan. No real reason. We just followed our hearts and went where it felt like home.

Large crowd gathered outdoors at the Swinging in the Street event in downtown Winona Minnesota

I Found a Home…in Winona, Minnesota

So this past weekend, I wandered around 3rd and Center Streets, just taking it all in. I watched the dancers – swinging to jazz, bopping to a polka, waltzing in Winona – and I realized something. I finally found what I’ve been looking for every since I was a kid, crawling through my attic, listening to my great grandpa’s old timey records.

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I found the place that was simple, were time moved slow and folks were kind. I found a home…in Winona, Minnesota.

Poster for Swinging in the Street in Winona Minnesota

Video Tour with Jack and Kitty

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Swinging in the Street - Winona, Minnesota's Dance Party - Travel Memoir & Video Essay

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