Cottonwood County (pop. 11,687), west of Watonwan County, was named for the Cottonwood River, which was named for the trees along its banks.
The northeastern part of the county is drained by the Cottonwood River, which flows into the Minnesota River and then the Mississippi; the southwestern part of the county is drained by the Des Moines River, which joins the Mississippi at Keokuk, Iowa.
Des Moines River watershed
The county seat is Windom (pop. 4,646).
Cottonwood County Courthouse (1904)
The Des Moines River runs through Windom; the river is popular for canoeing and kayaking.
In winter there’s a Darn Cold Croquet Contest.
Near the town of Jeffers (pop. 369) is the Jeffers Petroglyphs Historic Site, with more than 2,000 images made by Native Americans over thousands of years on a large rock outcrop.
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Ask JP if cousin Cullen lived in Windom. Rings a bell but that may not be the right one. The petroglyph is intriguing, there’s a similar one along here on the Columbia.