Nothing Ever Changes in Winona, Minnesota

Written byJack and Kitty

Take a nostalgic journey through Winona, Minnesota’s history as we delve into a collection of captivating vintage photos. Join us as we explore the city’s iconic landmarks, cherished moments, and forgotten stories, offering a captivating glimpse into Winona’s past.

Nothing Ever Changes in Our Hometown

Interested in Winona, Minnesota’s history? We live in the small Mississippi River town of Winona. It sits about two hours south of the Twin Cities. Jack went to Winona State University and after years living in Minneapolis, Nashville, Tulsa, Burlington (and all points in between), it’s been fun coming back to this small college town.

In the coming months we’ll be sharing a lot more travel videos that we filmed here in Winona. There are some great hidden gems in this town and it’s definitely worth a weekend getaway from the hustle and bustle of Minneapolis and St. Paul.

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Last week we were digging around an antique store here in Winona. It’s an old brewery with caves dug into the side of Sugar Loaf bluff. We picked up a neat calendar published by the Winona County Historial Society. It’s a freebie that you can grab at newsstands with other local tourism pamphlets and brochures. There are some really neat pictures – all of which you can find at their museum. We thought it’d be fun to share them with you because they are really cool pictures from Winona back in the day.

If you’re a local reading this, you might get a kick outta these pix…and if you’re considering a visit, know this: most of the town looks exactly the same as when these pix were taken…nearly 100 years ago!!

Maybe whenever the snow melts we’ll wander the town and take some side-by-side pix so you can see exactly what we’re talking about. But first it needs to get warmer! Hehe.

If you find yourself in town and have a few hours to kill we really recommend a visit to the Winona County Historical Society. We’ll be sharing a vlog on our YouTube channel soon!

Vintage Photos of Winona

Winona, Minnesota's history
“Franklin and Third Streets in downtown Winona, Minnesota after a snowstorm. The Watkins building’s tower and smokestack can be seen in the background.”
Winona, Minnesota's history
“A horse drawn mobile home on East Second Street with the Latsch building in the background in Winona, Minnesota.”
Winona, Minnesota's history
“A black and white postcard of an aerial view of Winona, Minnesota at 13,000 feet. Did you know the Winona County Historical Society currently has over 1,730 postcards?”
Winona, Minnesota's history
“During the 1965 flood the Mississippi River crested at 22.77 feet at Winona by April 19, spilling into downtown and residential Winona. The current levee and dike system was developed because of the record water level and still protects the “Island City” of Winona, Minnesota today. This image, one of many in the WCHS collection, shows the water on Johnson Street looking toward the river.”
Winona, Minnesota's history
“Washington School’s May Day celebration in 1915. Washington School was on 4th Street between Zumbro and St. Charles Streets in Winona, Minnesota.”
Winona, Minnesota's history
“The “Houseboat Hobos” were a group of friends from Winona, Minnesota who, during the early 1900s, vacationed along the river.”
Winona, Minnesota's history
“View of the 1909 Winona Free Street Fair at the corner of 3rd and Lafayette Streets. Yes, those are two men in an elephant suit on a high wire!”
Winona, Minnesota's history
Here’s that same block from an alternate angle…this pic was taken nearly 70 years later! Most of these beautiful buildings are still standing today. This pic is from our collection. Courtesy of Jack and Kitty Norton.
Winona, Minnesota's history
“Black and white postcard of a float advertising St. Charles Mercantile Company in St. Charles, Minnesota.”
Winona, Minnesota's history
“The first kindergarten class in the “new” Madison School in 1933, which still stands on West Wabasha Street in Winona, Minnesota.”
Winona, Minnesota's history
“People posing on Eagle Bluff overlooking Trempealeau, Wisconsin. Photo by Winona photographer Charles Tenney, one of the more celebrated landscape photographers of the late-1800s in Minnesota. WCHS has over 700 images by Charles Tenney in their collection!”
Winona, Minnesota's history
“The Bear Creek Trestle near Rollingstone, Minnesota. Circa 1888.”
Winona, Minnesota's history
“Photograph looking east on 3rd Street between Johnson and Main Streets in downtown Winona, Minnesota. Shops seen in the print are the Conrad Fur Store on the left and Brown Drug Store on the right.”

Grab Your Calendar!

Unless otherwise noted, images in this blog post are from the “Favorites from the Photograph Collection Project”, a free calendar published by the Winona County Historical Society. Pick up a physical copy at WCHS or at pretty much any news stand or small business here in town. Recently, the Society completed a 16-month project to preserve and protect their amazing photograph collection. Over 12,000 images were scanned, plus they reorganized and properly stored thousands more.

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Exploring Winona, Minnesota Through Vintage Photos: A Step Back in Time

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Jack and Kitty Norton are Emmy Award winning and best-selling authors. High school sweethearts turned married soulmates, this fun-loving couple lives in the small college town of Winona, Minnesota and would love to have you over for some tater tot hotdish.

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