Sugar Loaf in 1950. Take a step back in time to the good ol' days with these vintage postcards from Winona, Minnesota – a charming town that never changes!

Vintage Postcards Offer A Glimpse Into The Unchanging Charm Of Winona, Minnesota

Take a step back in time to the good ol’ days with these vintage postcards from Winona, Minnesota – a charming town that never changes! 📬 #WinonaPostcards #VintageCharm #WinonaMN

Winona, MN – There’s something special about Winona, Minnesota – a quaint Midwestern town that seems to be frozen in time. Our home town is the kind of place where folks still greet each other on the street with a warm smile and a friendly wave. The air is crisp and clean, and the pace of life is just a little bit slower. It’s no wonder that people who are tired of the hustle and bustle of modern life find themselves drawn to this charming little southern Minnesota town, located just about two hours down the Mississippi River from Minneapolis.

If you want to get a feel for what Winona was like in the good old days, all you have to do is take a look at some of the vintage postcards from our personal collection. These postcards show a town that hasn’t changed much at all. The main street is still lined with mom-and-pop shops, and the local movie theater still uses real butter on their popcorn. It’s the kind of place where you can sit on a bench in the park and watch the world go by without a care in the world.

Looking at these postcards, it’s easy to see why so many people are drawn to Winona. It’s a place where you can escape the stresses of modern life and enjoy the simple pleasures that have been around for generations. Whether you’re taking a stroll down memory lane or discovering Winona for the first time, these vintage postcards are sure to put a smile on your face and a warmth in your heart. Here’s some our faves…

Vintage postcard from Winona, Minnesota. The Winona County Club offered wonderful golfing. Postmarked: 1949.

The Winona County Club offered wonderful golfing. Postmarked: 1949. You know there’s still excellent golfing here in Winona, MN! There’s even a year-round indoor course today.

Vintage postcard from Winona, Minnesota. The Hot Fish Shop near Sugar Loaf. Undated.

The Hot Fish Shop near Sugar Loaf. Undated. Locals still talk about how awesome this place was. I wish we had gotten a chance to try it. Thankfully, Winona still has some pretty awesome restaurants.

Vintage postcard from Winona, Minnesota. Third Street in downtown Winona. Circa: 1910.

It’s no secret that Winona has some awesome shopping. This is what Third Street in downtown Winona looked like in 1910 – and it looks almost the same today! Plus, it’s still drawing shoppers to downtown. You can even take some cool selfies while you’re here!

Vintage postcard from Winona, Minnesota. A birds-eye view of downtown Winona. Circa: 1910.

Here’s a birds-eye view of downtown Winona from 1910, and guess what? Most of these buildings are still around! You can see where (modern day) local faves Heart’s Desire and Blooming Grounds are in this pic. Heck, you can even see where I’m sitting writing this to you today! Whoa. Trippy!

Vintage postcard from Winona, Minnesota. Lake Side Drive and Sugar Loaf. Undated.

An undated postcard of Lake Side Drive and Sugar Loaf. Guess what? No surprise here: Sugar Loaf remains standing strong and is the iconic symbol of our awesome town! Did you know today you can shop at an antique store that is part of the caves under Sugar Loaf?

Vintage postcard from Winona, Minnesota. Latsch Island when it was known for its tourist camp and bathing beach. Circa: 1925.

Our office windows look towards Latsch Island, and although these structures from 1925 are gone now, Latsch Island remains a popular spot today for swimming, hanging out at the beach and exploring. There’s even a cool houseboat community that calls this island on the Mississippi River home!

Vintage postcard from Winona, Minnesota. The Happy Chef Restaurant and Pancake House was located at the junction of Highways 14 and 61. Circa: 1960s.

The Happy Chef Restaurant and Pancake House was located at the junction of Highways 14 and 61. This postcard is from the 1960s. Today, my fave spot for tasty breakfast treats in Winona is Curiosi-Tea House or Bloedow Bakery. Yummmmmy!

Vintage postcard from Winona, Minnesota. Bub's Beer on the Mississippi River. Circa: 1960s.

What sounds better than a Bub’s Beer on the Mississippi River in the heart of the summer? Well, even though this pic is from the 1960s, you can still visit Bub’s Brewing Company on 4th Street in downtown Winona today!

Vintage postcard from Winona, Minnesota. St Stanislaus Church from the corner of Carimona and Fourth Streets. Circa: 1960s.

A postcard from the 1960s of St Stanislaus Church on the corner of Carimona and Fourth Streets. Wanna visit St. Stan’s today? You should it’s amazing! My hubby Jack even made a little video tour so you can visit St. Stan’s from wherever you are!

Vintage postcard from Winona, Minnesota. The campus of St. Mary's College. Postmarked: 1945.

This one is postmarked 1945 and it’s of the campus of St. Mary’s College. And yup, you guessed it: St. Mary’s is still rockin’ and rollin’ and is currently very, very haunted! If you love spooky stuff, don’t miss our post all about the haunted hotspots of Winona, MN!

Vintage postcard from Winona, Minnesota. The back of this postcard reads: "Sugar Loaf Mountain, seen from municipal swimming beach appears to be what its name implies. Towering majestically above this thriving industrial city, it is admired by residents and visitor alike." Dated: 1950.

The back of this 1950 postcard reads: “Sugar Loaf Mountain, seen from municipal swimming beach appears to be what its name implies. Towering majestically above this thriving industrial city, it is admired by residents and visitor alike.” I could not have said it better myself. And I just returned from a walk around Lake Winona and stood at this very spot earlier this morning! Beach is gone, walking/cycling path is here now and is amazing. Don’t miss the blooming of the cherry trees every spring!

Vintage postcard from Winona, Minnesota. Wisconsin End of High Wagon Bridge over the Mississippi River. Dated: 1910.

I love this postcard from 1910 of the Wisconsin End of High Wagon Bridge over the Mississippi River. Of course, fashion has changed a bit: thankfully I don’t need to wear a petticoat every time I leave the house! Hehe. So what remains the same? The heart of Winona. It’s beating at a simple, steady pace. A place where time slows down, folks still smile and life is lived as it was meant to be: full of laugher, joy and community.

I hope you enjoyed this simple stroll down memory lane! My hubby Jack and I have tons more postcards like this so let me know if you’d like another post with some more vintage treasures. Have a super day!

🗣 Which postcard did you like the most? Do you have any unique collections like this? We’d LOVE to hear from you in the comments section below. ⬇️

SHARE This Minnesota News Article With Family And Friends…

Leave a Friendly Comment or Thought