In 1860 it took about three hours by horseback to cover the 24 miles between the Woodsmall-Mount-Dowden farm at Floyd’s Fork near LaGrange, Oldham County, Kentucky and cousin Stephen May Woodsmall’s plantation in Middletown, Jefferson County, Kentucky. The Floyd’s Fork farm was purchased by James William Woodsmall in 1814. His younger brother, “Captain” John Woodsmall, was one of the founders of Middletown about the same time after he came back from the War of 1812. The physical distance was short, but the trip crossed an historical family divide between north and south, between anti-slavery and pro-slavery and between the Union and the Confederacy.
The issue of slavery affected the lives of James and Nancy Woodsmall and their nine children: George Lasley Woodsmall, Sr., Margaret, Henrietta, James William, Lettice, Elizabeth, Jefferson Hezekiah, John and Nancy.
Tithables and Tax List data from 1782 to 1796 appear to indicate that the Woodsmall patriarch, James, was not a slave owner. Whether he was not by conviction or economic circumstances is not clear. While many of his immediate neighbors on Simpson’s Creek, Nelson County, Kentucky (Virginia until 1792) owned slaves, the census data corroborates that the Woodsmalls did not own slaves.