Ragged Branch was started in 2014 by Alex Toomy, a Virginia real estate developer, with partners Russell Nance and Chris Sarpy on a farm outside Charlottesville, after the 2009 downturn hit Toomy's real estate business. The late Dave Pickerell, former master distiller of Maker's Mark, guided the founders and helped develop the mash. The distillery grows all of its grain on owned or leased land, mills it fresh each day, ferments for about four days and distills in a copper pot-column still before aging in new charred oak, and spent mash goes to feed the farm's cattle. Its first Virginia straight bourbons, one wheated and one with rye, went on sale in fall 2017. In 2025 production moved to Toomy's childhood farm in Augusta County near Waynesboro, while the original Charlottesville farm now operates as the 92 Acres tasting room; the company remains privately owned and run by its founders.