[3] The county name was taken from the village name, which is said to derive from a Dakota legend about a woman, Winona, (a relative of Chief Wabasha) who was betrothed to a warrior she did not love.

Winona County lies on Minnesota's border with Wisconsin and is part of the driftless area that defines southeastern Minnesota, northeastern Iowa, southwestern Wisconsin and northwestern Illinois.

The Mississippi, flowing south-southeast, defines the county's eastern border.

The U.S. Army Corps of Engineers (St. Paul District[7]) maintains the lock and dam system in this region.

The county terrain consists of low rolling hills with the east portion particularly etched by drainages, and lightly sprinkled with lakes.

In 2016, Winona County planning commissioners voted to approve new permits for existing commercial dog breeding operations, also known as "puppy mills", despite overwhelming evidence of animal cruelty and neglect.

[19] The US Census Bureau ranked this μSA as the 591st most populous Core Based Statistical Area of the United States as of April 1, 2020.

In the 2022 elections, Winona County voted for the Republican nominee for all statewide offices.

Jeremy Miller (R) and Steve Drazkowski (R) represent it in the Minnesota Senate.

Winona County is in Minnesota's 1st Congressional District, which is represented by Brad Finstad (R).