In a state where bourbon is often associated with Kentucky hills rather than North Carolina streets, a group of Durham natives is building a brand rooted as much in memory and heritage as in oak barrels and mash bills.
For Jesse Carpenter, chief product officer and co-founder of Old Hillside Bourbon, the venture is inseparable from place.
“This is Durham. This is where I’m from. This is where I grew up,” Carpenter said in a recent interview, reflecting on the city that shaped both his upbringing and his entrepreneurial ambitions.
A Name Steeped in History
The company draws its identity from Hillside High School, one of the oldest historically Black high schools in the United States. The founders — Carpenter and several childhood friends — are graduates of the school’s Class of 1993, back when Hillside stood at Concord and Lawson streets in what alumni still call “the old Hillside.”
“We graduated Class of 1993 from Hillside High School,” Carpenter said. “Concord and Lawson Street. It’s the old Hillside.”
Hillside High School traces its roots to the late 19th century, emerging during Reconstruction as educational opportunities for Black students expanded despite the constraints of segregation. Over generations, the school became a pillar of Durham’s Black middle class, producing educators, civic leaders and entrepreneurs who would shape the city’s identity.
Old Hillside Bourbon’s founders say they wanted the brand to carry that legacy forward — not simply as nostalgia, but as narrative.
A Pandemic Idea Becomes a Business
The idea for the company took shape during the isolation of the COVID-19 pandemic, when long-standing friendships were rekindled and new ventures imagined.
“I had an idea to start a bourbon company, and they were on board,” Carpenter said. “Friends from 30 years ago, and now we’re doing this business together. It’s awesome.”
In its inaugural year, Old Hillside distributed approximately 300 cases. This year, the company projects distribution of 10,000 cases — a more than thirtyfold increase that reflects both expanding retail partnerships and a growing appetite for craft spirits.
The brand earned national attention when it took Best in Show honors at the 2023 TAG Global Spirits Awards, a competition judged by industry professionals and seasoned tasters. Reviews from independent outlets, including the Bourbon Banter YouTube channel, praised its layered aroma and balanced finish, citing notes of oak and vanilla — hallmarks of well-aged American bourbon.
Like many premium bourbons, Old Hillside is distilled and bottled in Kentucky, the historic epicenter of American bourbon production. According to the Kentucky Distillers’ Association, 95 percent of the world’s bourbon supply originates in the state, benefiting from its limestone-filtered water and longstanding distilling infrastructure.
Yet Carpenter is quick to emphasize that while the liquid may be Kentucky-made, the brand’s soul is Durham-born.
A Bottle as Archive
Each release of Old Hillside Bourbon doubles as a cultural artifact.
The inaugural bottle features an image of the original Hillside High School building, anchoring the brand in local memory. A subsequent expression pays tribute to African American jockeys who dominated the early years of the Kentucky Derby before being systematically excluded during the Jim Crow era. Historians note that 15 of the first 28 Kentucky Derby winners were Black jockeys — a legacy largely erased from mainstream narratives.
The company’s latest release honors the Harlem Hellfighters, the famed all-Black 369th Infantry Regiment that served with distinction in World War I. Denied equal treatment at home, the regiment spent more time in continuous combat than any other American unit in the war and received France’s Croix de Guerre for valor.
For Carpenter and his partners, these design choices are intentional. The bottle becomes not just a consumer product, but a vessel for stories that might otherwise go untold.
“We want every vintage to say something,” Carpenter explained. “We want people to learn something.”
Building a North Carolina Footprint
Brand ambassadors Corey Carpenter and Amire Schealey are working to expand Old Hillside’s presence across North Carolina’s tightly regulated spirits market. In the state, liquor sales operate through a control system managed by local Alcoholic Beverage Control (ABC) boards, requiring brands to navigate approval processes and cultivate relationships market by market.
“More bars and restaurants — tackling different markets,” Corey Carpenter said. Schealey added that the team is organizing tastings at various ABC boards to increase visibility and consumer awareness statewide.
North Carolina’s craft spirits industry has grown steadily over the past decade, bolstered by legislative reforms that expanded tasting room privileges and distribution opportunities. According to the North Carolina Distillers Association, the number of craft distilleries in the state has multiplied since 2010, reflecting consumer demand for locally connected brands.
Old Hillside’s founders see themselves as part of that movement — even if their product is distilled across state lines.
A Durham Story in a Kentucky Barrel
In Durham, a city that blends tobacco-era industrial history with a new generation of entrepreneurs, the brand fits within a broader renaissance of Black-owned businesses reclaiming and reinterpreting local heritage.
“Old Hillside is a lifestyle,” Jesse Carpenter said. “Not just a school — friendship and camaraderie. That’s what we do.”
For the founders, the bourbon is less about competing in a crowded spirits market and more about honoring a shared origin story: classrooms on Concord Street, friendships forged in adolescence, and a city that continues to shape its sons long after graduation.
As Old Hillside expands from hundreds to thousands of cases, its founders insist that growth will not come at the expense of identity. Each label will continue to carry Durham’s imprint — a reminder that even in a Kentucky-distilled spirit, the truest ingredient can be memory.
The Bull City Citizen will continue spotlighting Durham-made enterprises and the entrepreneurs who are redefining what it means to build locally while thinking nationally.
