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The local upper school, Ashby School, previously Ashby Grammar School, is a mixed comprehensive school for 14 to 19-year-olds and has its roots in the 16th century.
Dolly Shepherd, 1887-1983, the famous Victorian aviatrix, made her return to parachuting from balloons in a display at Ashby, after recovering from a potentially fatal accident.
Ashby was home to the video game software house Ashby Computer Graphics, also known as Ultimate Play The Game, now called Rare.
Ashby became a planter and a businessman, amassing a considerable fortune.
General Thomas E. "Stonewall" Jackson, under whose command Ashby served, declared that he "...never knew [Ashby's] superior as a partisan leader." Ashby was killed in a skirmish on Chesnut Ridge near Harrisonburg, Virginia, on June 6, 1862, the eve of the climactic battles of Cross Keys and Port Republic.
Ashby and his men were fighting a rear guard action against the Yankees in an attempt to buy time for General Richard Ewell to set his defenses.