America's Best Small TownsMain streets worth the drive, region by region
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Brick storefronts along the historic main street of Wabasha, Minnesota, at sunset

Small Towns of the Midwest

Great Lakes islands, Mississippi bluffs and Ohio River main streets.

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Small Towns in the Midwest

The Midwest’s best small towns sit on water: the Great Lakes, the Mississippi, the Ohio. They are brick main streets with river views, lake islands without cars, and farm towns that turn into festival towns for a weekend each year.

Michigan: Mackinac Island and Holland

On Mackinac Island, motor vehicles are banned, so the soundtrack is horse hooves and bicycle bells. Visit Fort Mackinac, cycle the road around the island’s shore and, of course, buy fudge. On Lake Michigan, Holland celebrates its Dutch roots with the Tulip Time festival each May and a working Dutch windmill, De Zwaan, on Windmill Island.

Wisconsin and Illinois

Door County, the peninsula between Green Bay and Lake Michigan, is a string of small villages — Fish Creek, Ephraim, Sister Bay — with lighthouses, cherry orchards, Peninsula State Park and traditional fish boils. In northwest Illinois, Galena preserves a 19th-century main street and the home given to Ulysses S. Grant after the Civil War.

Minnesota’s river towns

Along the Mississippi, Wabasha is home to the National Eagle Center, where you can see bald eagles up close and often spot wild ones over the river in winter. Upriver, Red Wing sits below the bluffs and is known for its boots and stoneware. Inland, Lanesboro is a base for the Root River State Trail, a paved bike path through bluff country. For Stillwater, Duluth and the North Shore, see Best in Minnesota.

Lanesboro, Minnesota from above

Indiana and Ohio

On the Ohio River, Madison, Indiana, has one of the Midwest’s largest collections of 19th-century buildings and the Lanier Mansion State Historic Site. Neighboring Vevay was settled by Swiss immigrants and still celebrates that heritage with its Swiss Wine Festival. In Lake Erie, Put-in-Bay on South Bass Island is home to Perry’s Victory and International Peace Memorial.

Bluffs above the Mississippi at Red Wing, Minnesota
Red Wing, Minnesota, sits between the Mississippi River and its bluffs.

Midwest Towns by Season

SeasonTownWhy then
SpringHolland, MITulip Time festival in May
SummerMackinac Island, MI; Door County, WIFerries, lake swimming, cherry season
FallGalena, IL; Madison, INFoliage over river valleys and historic streets
WinterWabasha, MNBald eagles gather on open stretches of the Mississippi

Frequently Asked Questions

Can you drive on Mackinac Island?

No. Motor vehicles have been banned on Mackinac Island for more than a century. You arrive by ferry from Mackinaw City or St. Ignace and get around on foot, by bicycle or by horse-drawn carriage.

Which Midwest small towns won USA TODAY 10Best in 2026?

In the 2026 Readers’ Choice vote for Best Small Town in the Midwest, Vevay, Indiana, placed first and neighboring Madison, Indiana, second, according to Madison’s tourism office. Madison had won the category in 2024 and 2025.

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