Born and raised in Madisonville, Kentucky—which is to say, in the cradle-state of bourbon—brothers Jason and Jerrad Oakley had a long and winding road to Anderson, Indiana, where they’ve set up their distillery in a century-old building that at one time functioned as a Studebaker dealership. The adventurous pair tinkered with recipes in a South Carolina garage; discussed their dreams of distilling during a hiking trip to Machu Picchu; and sealed the deal on a Smoky Mountains motorcycle jaunt.
“We had a tire blow out in the middle of nowhere at night,” Jerrad recalls. “As we were waiting for the tow truck to arrive, we had the ‘Are we really going to do this?’ conversation and hashed out the details.”
Jason was already living in Indiana at the time and after securing the Anderson location, the duo devoted themselves to completely gutting and renovating the languishing site, tearing out the equivalent of three houses worth of debris, plumbing, and wiring. They opened the doors to Oakley Brothers Distillery in 2018; today, the spacious facility accommodates a cocktail bar, production operations, food service, and event space.
The first product out of the gate was Indiana Moon moonshine, followed by an apple pie-spiced variation that remains a best-seller to this day. However, the Flyover Whiskey is the Oakleys’ signature product.
“It really evolved from the Indiana Moon white dog,” Jerrad says. “We use white oak barrels and add a selection of staves for a caramelly-vanilla finish.”
The Oakley portfolio also includes 317 Vodka, Mutiny Rum, Hell or Rye Water, 765 Gin, and a limoncello. The brothers are also looking to revive an oatmeal bourbon recipe they produced early on, and plan on barreling a 22-grain bourbon in the near future.
“We make an absinthe using an 1850s recipe we picked up in Europe,” Jerrad adds. “It is phenomenal, but for a daily sipper, I love our Uno Mas agave spirit with a little ice.”
Customers can sample the wares straight up, in a flight or mixed into craft cocktails at the distillery (the Blackberry Smash is the most-requested order). Oakley has recently started canning cocktails as well, but the rest of their offerings, these can be difficult to source. They’re worth the hunt.