Originally established by Elijah Pepper, the distillery was passed on to his son and became known as the Oscar Pepper Distillery when Dr. James Crow worked there in the mid-19th century. The distillery was sold to Brown-Forman who operated it until the late 1960s, then sold the property to a local farmer. Brown-Forman re-purchased the property in 1993, refurbished it, and brought it back into operation. The Woodford Reserve brand was introduced to the market in 1996.
The distillery produces Woodford Reserve Bourbon, Woodford Reserve Double Oaked, Woodford Reserve Straight Rye Whiskey, Woodford Reserve Straight Malt Whiskey, and Woodford Reserve Wheat Whiskey. It also distils some limited-edition releases, including Woodford Reserve Master's Collection, Woodford Reserve Master's Collection Batch Proof, a Kentucky-only Distillery Series, and a special commemorative bottle it releases annually in conjunction with its official sponsorship of the Kentucky Derby.
Woodford Reserve won a double gold medal each time at the San Francisco Spirits Competition. It has also won gold (2006–2007, 2011–2012) and silver (2008, 2010) medals at this annual event.