Touring the James E. Pepper Distillery in Lexington, Kentucky

The day after our stop at the Wigle Distillery in Pittsburgh, we headed south through West Virginia and Kentucky.  After stopping for lunch with Dan's family, we pressed on to Lexington, arriving late on a Sunday afternoon with just enough time for one tour before the distilleries closed down for the day.  

The distillery we chose was the James E. Pepper Distillery. It bears the Kentucky distillers permit DSP #5, the fifth license issued by that state. That license number is a bit deceiving though, because what was once one of the largest and oldest distilleries in Kentucky is now a relatively small craft distillery that has only been "back" in operation since 2008.

We arrived without a reservation, but were lucky enough to pick up one of the last tours of the day at 4:00, and since we had a few minutes to wait, we started off with an Old Fashioned from the Distillery's tasting room.  Why an Old Fashioned?  One of the cocktail's origin stories is a claim by the Louisville-based  Pendennis Club that a bartender there created the cocktail in honor of none other than the prominent distiller James E. Pepper.  Like so much of bourbon history, this claim is disputed, as the cocktail was described in the Chicago Tribune a year earlier in 1880 and there are indications that the mixing of spirits, water, sugar and bitters for the creation of cocktails goes back to as early as 1833.  

Early Pepper Distillery History

Jessie starts off the tour in the museum.

Our tour began in the Distillery's museum, a room just off to one side of the tasting room and bottle shop which features many artifacts from the distillery's history.  Our guide, Jessie, was embarking on his first ever solo tour, but he had clearly learned his business well and was animated and fun right from the beginning. More importantly for us, he was gracious to the whiskey know-it-alls at the back who answered almost every question he asked (after first giving others a chance, of course!)

The first Pepper to distill spirits in America was Elijah Pepper, who began distilling whiskey in Virginia in 1780, while the American Revolution was still ongoing. Elijah's connection to the revolution was later used in branding the company's whiskey "Old 1776," and is the namesake of today's 1776 bourbon and rye brands, which so far have been produced on a contract basis. Today's distillery also produces a white dog brand called "Old Elijah Pepper" in honor of the first family distiller.

After the Revolution, Elijah established his distillery in Versailles, Kentucky in what is today the Woodford Reserve Distillery.  After his death, the Distillery passed to his son Oscar, who continued to be operate the distillery through the Civil War.  Oscar who hired Scottish Chemist James Crow, and the two men perfected the sour mash method there at the Versailles facility. During this time, the two men were producing whiskey under the Old Crow brand that today belongs to Jim Beam, and it was this whiskey which was a favorite of Ulysses S. Grant, Andrew Jackson, Henry Clay and Daniel Webster.

Oscar died suddenly in 1865, and the distillery passed to his son, James.

James E. Pepper and his Remarkable Wife

James inherited the distillery at the young age of 15, and he continued to manufacture whiskey at the Versailles distillery initially, expanding it with a loan provided by Colonel EH Taylor.  

Unfortunately, in what was the first of many financial struggles for James, he failed to pay back the loan, and Taylor foreclosed on the distillery and sold it.  

A year later, James raised the money to build a new distillery on the site of the current James E. Pepper distillery in Lexington, Kentucky.  While making whiskey at this facility, James lobbied the Kentucky legislature and successfully changed state law so that he could bottle whiskey at the distillery to ensure quality.  He added a paper seal bearing his signature, ensuring his customer of a pure, quality whiskey not tainted by unscrupulous rectifiers.  During this time the distillery's leading brand was Old Pepper, which is currently being used with the rye whiskies distilled at the Lexington facility.

Ella Offut Pepper 
Courtesy:
Wikimedia Commons

James was a flamboyant promoter and horseman with a stable of thoroughbred horses and a private railcar promoting his brand.  His flamboyant promotion made the Pepper brand successful for a 20 year period, but unfortunately left him deep in debt and facing bankruptcy in when the whiskey market went bust in 1890.  The Distillery and his horses were put up for auction to cover his debts.

Luckily for James, his wife Ella Offut Pepper was a formidable woman.  She was the highest bidder for the horse farm, since no one in Lexington would bid against her.  She took up horse racing and breeding, and was able to raise sufficient funds from the sale of her horses to purchase the distillery out of foreclosure and return it to operation. 

James and Ella enjoyed continued success racing all over the world and continued to produce one of the nations leading whiskey brands for another decade, making frequent trips to the Waldorf-Astoria hotel in New York City, and supposedly bringing the recipe for the Old Fashioned Cocktail to the Hotel.  James died in 1905 after slipping on an icy New York sidewalk, and Ella sold the distillery and most of the horses.

Under new ownership, the distillery continued to operate into the 1960's, even making whiskey under a medicinal license through Prohibition.  Like so many of the country's old whiskey brands, however, the Pepper distillery could not survive the hippie generation's rebellion against their parents.  It ceased production in 1967.

Rebirth of the James E. Pepper Distillery

This Johnson-Jeffries fight picture launched Amir Pey's 
search to discover and relaunch the James E. Pepper brand.

Entrepreneur Amir Pey discovered the Old Pepper brand while studying photos of the great Johnson - Jeffries boxing match of 1910.  He wondered about how this whiskey brand that he had never heard of was promoted so prominently in one of the most prominent athletic contests of its day, and began researching the brand and collecting the memorabilia that graces the distillery museum today.

Pey acquired the Lexington distillery site and rebuilt it. He was even able to obtain the rights to the original distiller's license DSP number 5.  The distillery barreled its first whiskey in 2017, using the same mash bills that were in use 50 years earlier when the distillery closed.  

Trevor, Dan, and Mitch with the James E. Pepper Still

The first whiskies available from the present-day Pepper brand are the 1776 Bourbon and 1776 Rye, which to-date have been contract distilled off-site.  These whiskies are available in 26 States today, including here in Maine.  At the distillery, we were also able to purchase cask strength versions of the 1776 products, as well as a single barrel Old Pepper Distillery Rye and Elijah Pepper white dog.  

When people ask about our favorite tours on the Kentucky bourbon trail, this one always ranks among the top three alongside Limestone Branch and Castle and Key.  There are tons of reasons for that:  Jessie's energy and enthusiasm are important as well as the small intimate group we were in and the opportunity to do things like taste the fermenting distiller's beer, or taste the bourbons straight from the barrel are big common threads among the best tours.  Another is a compelling story, and the James E. Pepper story a dramatic one that touches both the American Revolution and the central figures of the Civil War.  It is also an amazing story of perseverance, with multiple crises resulting in the brand's death and rebirth.

Tasting James E. Pepper Products

During the tour, we had the chance to taste whiskey that Jessie drew directly from the barrel with a thief, after which, he brought us in to a private tasting room to try some additional whiskey before the end of the tour. While we were there, we got to taste the 1776 Flagship Bourbon and Rye as well as the cask strength versions of those spirits and three different variants of the Old Pepper Distillery Rye.  

This post has already run pretty long, so I'll save James E Pepper tasting notes for another post. For now, suffice to say that the Old Pepper Distillery Rye, batch 18, barrel 80 was our favorite pour of the day.  Each of us left with at least one bottle of it, and we ended up returning for more later in the week.  The bottle was so good it ended up being our first bottle kill of the week, late that same evening on the back patio of the Hampton Inn.  If you get the opportunity to try Old Pepper, don't let it pass you by!