The area was part of the 100,000-acre (400 km2) grant in the early 1700s to the family of John Preston's wife, born Elizabeth Patton, which he administered on her behalf.

[9] On January 10, 1862, nearby Middle Creek National Battlefield was the scene of the largest battle of the Civil War to occur in Eastern Kentucky.

Country music stars including Loretta Lynn, Crystal Gayle, Wynonna Judd, Naomi Judd, Billy Ray Cyrus, Tom T. Hall, Ricky Skaggs, Keith Whitley, Dwight Yoakam, and Patty Loveless are all from the Big Sandy Valley.

23" (from his album Hillbilly Deluxe), a song about the yearning of local coal miners to escape their plight by traveling up U.S. Route 23 to find employment in the factories in the North, not knowing that they were only trading one miserable life for another.

Prestonsburg is the location of the Mountain Arts Center, which hosts music concerts and is home to the Kentucky Opry.

Middle Creek National Battlefield is the site of the largest and most significant Civil War battle in Eastern Kentucky.

Built by Samuel May in 1817, the house was used by the Confederate forces as a recruiting station during the American Civil War.

The Theatre's presentations of classic Broadway musicals, comedies, historical dramas and holiday productions kept theatre-goers entertained for over 40 years.

Prestonsburg is in northern Floyd County in the eastern part of the state, along the banks of the Levisa Fork of the Big Sandy River.