Best Small Towns in Midwest: Minnesota's Winona, Stillwater

There is nothing like a small town: the pace, the people, the lack of traffic; the list goes on and on. USA Today is celebrating the best small towns in the Midwest, and these two Minnesota towns need your help to reach the top.

Which small town is the best in the Midwest? That is the question USA Today is asking for its Readers' Choice Awards 2025. They’ve narrowed the list down to the top 20, and voting is open now to narrow that down even more.

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USA Today points out that the Midwest “happens to be home to some of the most charming, scenic, and historic small towns in the United States.”

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Minnesota is represented by two historic towns, Winona and Stillwater. Both have charming downtown areas filled with shops and historic buildings, both are located on rivers, and both are popular tourist destinations.

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Stillwater: The Birthplace of Minnesota

Located on the St. Croix River, Stillwater is often called the “birthplace of Minnesota.” In 1848, a territorial convention held there helped establish the state.

USA Today says Stillwater is “where in-the-know travelers go for scenic boat tours, historic charm, and plenty of fresh air.” All that is true; Stillwater has a unique charm to it and is a popular summer destination for many in the Midwest.

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Winona: A Gem on the Mississippi

Nestled next to the mighty Mississippi River, Winona is the second Minnesota town up for best in the Midwest. USA Today points out Winona’s proximity to scenic attractions like Sugar Loaf Bluff and the Garvin Heights Lookout, and the hiking trails at Great River Bluffs State Park.

USA Today also mentions Winona’s cultural scene: “The Minnesota Marine Art Museum, Winona Ice Fest, and Midwest Music Fest bring dynamic entertainment and showcase the town’s culture and persistent charm.”

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Cast Your Vote Before It’s Too Late

Voting for the best small town in the Midwest is open until 11 AM CST on Monday, March 31st, and the winning small towns will be announced on Wednesday, April 9th.