Surveyed in 1731 it was the first land tract (legally) patented by a Euromerican in what would eventually become Washington County.

On the opposite (west side) of Elk Ridge is the historic Kennedy farm where John Brown and his followers stayed prior to their raid on nearby Harpers Ferry, West Virginia.

A handful of John Brown's men escaped from the Federal soldiers after the raid was defeated, and the escape route that these men took went north to Pennsylvania following Elk Ridge and South Mountain.

Nestled at the foot of Elk Ridge on the west side of the lower valley is the community of Yarrowsburg, named for early (1830s) free African-American residents Aquilla and Polly Yarrow.

[2] During the Antietam Campaign of the American Civil War, Pleasant Valley was the site of a Confederate picket line, intended to prevent General George B. McClellan's Union Army from coming to the rescue of the Union garrison in Harpers Ferry.