The Kentucky Bend covers a land area of 45.472 km² (17.557 sq mi), according to the Census Bureau. The exclave was created due to the shift in course of the Mississippi after the New Madrid Earthquakes in 1811 and 1812. Surveyors marking the boundary between Kentucky and Tennessee had estimated where their line would meet the Mississippi; later, more detailed surveys revealed the division of the loop. The western border of Kentucky is designated as the Mississippi River, as is the eastern border of Missouri — thus the creation of a "notch" for Kentucky, but not for Tennessee.

The state of Tennessee contested the inclusion of the Kentucky Bend in the state of Kentucky, and it was legally part of Obion County, Tennessee, until at least 1848, but Tennessee eventually dropped its claim.

Due to its extremely fertile soil, Kentucky Bend was once a major cotton-producing area. The 1870 census found more than 300 residents. In The West Tennessee Farm edited by Marvin Downing (University of Tennessee at Martin Press, 1979), Norman L. Parks reports that in 1880 there was a population of 303, of whom 18 were African American. By 1900, there were "large numbers of Negroes (sic) in the Bend" to plant and harvest the cotton.

This area of the Mississippi River, from just east at "Island Number Ten" around to the town of New Madrid, Missouri, was the site of a Civil War battle from February 28 to April 8 1862, the Battle of Island Number Ten.

In Mark Twain's book Life on the Mississippi, he reports on the six-decade long feud between the Darnell and Watson families and other elements of life in the Bend. "In no part of the South has the vendetta flourished more briskly, or held out longer between warring families, than in this particular region,” he wrote. Twain continues:

Both families belonged to the same church ... They lived each side of the line, and the church was at a landing called Compromise. Half the church and half the aisle was in Kentucky, the other half in Tennessee. Sundays you'd see the families drive up, all in their Sunday clothes, men, women, and children, and file up the aisle, and set down, quiet and orderly, one lot on the Tennessee side of the church and the other on the Kentucky side; and the men and boys would lean their guns up against the wall, handy, and then all hands would join in with the prayer and praise; though they say the man next the aisle didn't kneel down, along with the rest of the family; kind of stood guard.

The mailing address of the area is Tiptonville, Tennessee.

In April 1981, author Allen Anthony wrote an article for The Filson Club Quarterly entitled "Kentucky Bend: A Struggle for Political Identity."

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