Our Story
In 2023, my father and I decided to pursue a whiskey venture. We each had different ideas starting out, as I’m well versed in whiskey and my father is a French wine and brandy enthusiast, but ultimately decided upon blending and occasional cask finishing as a means to meet in the middle.
Our first project involved choice Pineau de Charentes and Armagnac casks shipped directly from France to Kentucky. Initially, the process was intensive, but in time I began to understand how each cask enhanced the whiskey. I stayed attentive, making sure the essence of the original spirit remained intact. After many months, the whiskey was ready, and early in 2025 we completed our first bottling. All that was needed was the right brand – something that encompassed both American and French artistry with a family touch, and thus, Caleb’s Crossing Whiskey Company was born.
Looking to the Past
My father and I descend from Caleb Jennings (1759-1816). Based on Virginia genealogical records, the Jennings family moved from Orange County to Goochland County in 1766. After his father’s passing in 1773, Caleb became an indentured apprentice for an Orange County leatherworker and later enlisted in the Continental Army along with the sons of his master. He served in the Taylor’s Regiment of Guards at Charlottesville, Virginia until the end of the American Revolutionary War.
Listen to “Caleb’s Crossing” by The Bourbon & Rye Band!
In 1783, Caleb and his brother, Joshua, sold their family’s land in Goochland, moving from Virginia to North Carolina, and in short time, Georgia. The brothers each married and established homesteads but Caleb eventually purchased land in the French Huguenot settlement of New Bordeaux from the estate of a Frenchman, Jean Emery in Abbeville District, South Carolina.
While there is no evidence that Caleb distilled whiskey or brandy, it was a relatively common practice for 18th- and 19th-century farmers. There is, however, evidence of wine production in New Bordeaux, with dedicated vineyards noted on maps from the era. Living in the community, it’s safe to assume that Caleb and his family were exposed to various aspects of French culture, including French cuisine, wine, and spirits.
In 1783, Caleb and his brother, Joshua, sold their family’s land in Goochland, moving from Virginia to North Carolina, and in short time, Georgia. The brothers each married and established homesteads but Caleb eventually purchased land in the French Huguenot settlement of New Bordeaux from the estate of a Frenchman, Jean Emery in Abbeville District, South Carolina.
While there is no evidence that Caleb distilled whiskey or brandy, it was a relatively common practice for 18th- and 19th-century farmers. There is, however, evidence of wine production in New Bordeaux, with dedicated vineyards noted on maps from the era. Living in the community, it’s safe to assume that Caleb and his family were exposed to various aspects of French culture, including French cuisine, wine, and spirits.
Caleb’s Crossing
The sketches on our labels illustrate scenes from Caleb’s life in the 18th century, with the first depicting Caleb and his brother Joshua preparing to cross rivers and mountains on their journey to a new home. The copper coin draped over the neck of the bottle symbolizes the fares they would have paid ferrymen to cross unfordable rivers. The obverse of the coin mimics 18th-century coinage, with “CC” as an abbreviation for Caleb’s Crossing. The reverse of the coin, as well as the seal on the stopper, are a fife and drum representative of Caleb’s service in the American Revolution.
Farmer. Soldier. Pioneer. Our whiskeys are dedicated to the perseverance and pioneering spirit of Caleb Jennings and his family – a toast to perseverance and the spirit of exploration that embodies revolutionary spirits.
For more information on our expressions, please visit our Release Details page. Caleb’s Crossing is to be enjoyed neat, on the rocks, in a cocktail, or however you appreciate your whiskey. But regardless of your preference, always enjoy it responsibly.
À votre santé!
David Jennings
Curator & Blender