The largest and most well-known of these appears to have been Barney Ott's shop, where the local Farmer's Alliance held its meetings.

On October 18, 1863, Confederate Gen. John Imboden attacked Charlestown in an attempt to dislodge the Union troops garrisoned there.

Moving south along the Berryville Turnpike, Imboden was attacked by a union force that had advanced from Harpers Ferry.

“There were a number of killed and wounded on each side in this action.”[3] One of the largest engagements in Jefferson county between two cavalry units took place near Rippon during the Civil War.

On November 18, 1864, Union Captain Richard Blazer and his Independent Scouts were searching for Confederate Colonel John S. Mosby's Partisan Rangers.

Lieutenant Adolphus (Dolly) Richards, serving under Mosby, was leading a group of Rangers when he learned of Blazer's approach.

In 1900, a new one-room brick school for white students was built on the south side of Withers-LaRue Road.

Although some buildings have changed or disappeared over the past 100 years, Rippon still bears a strong resemblance to its appearance in the early 20th century.