The first Europeans to settle in the county were on Loutre Island perhaps as early as 1798, while the country was under control of Spain.
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The Katy Trail State Park, a 225-mile-long former railroad bed converted to public use, crosses the Loutre River at McKittrick by means of an iron truss bridge built by the A.P. Roberts Company in 1897.
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Graham Cave is a Native American archeological site near Mineola, Missouri in Montgomery County in the hills above the Loutre River.