Based on a true ‘bourbon’: Distillery continues to make footprints in Charlotte
After turning a hobby of making homemade whiskey into a local distillery business, buddies Matt Simpkins and Thomas Bogan believe great-tasting bourbon should come with a story.
They’re proud that the tale of Oaklore Distilling Co. in Matthews began right in the Charlotte region — with whiskey aged in barrels.
“These barrels are made of staves of oak, and each one comes from an oak tree that had a life and story,” Simpkins said. “The folks who enjoy our whiskey also have their own story. Whiskey is fun because your palate is your palate, and you’re going to taste different things that maybe I wouldn’t.”
Barrel by barrel, they established a business with a $12 million investment in the region and a growing presence around the Charlotte area. Oaklore celebrated its third anniversary this year, with more plans for growth ahead.
The spark for the business began about a decade ago when they would walk their children to the school bus stop. They both discovered a shared love for bourbon. They would blind taste bourbons and whiskeys to hone their palates and better understand the nuances of the spirits. Friends also joined in the fun.
“We eventually progressed to being able to taste and smell to determine the age,” Simpkins said. “We kind of nerded out on that. We ended up creating our own palate and understanding what it is that makes a really good and tasty product.”
Bogan said they didn’t come from the industry, but they wanted to build something they could be proud of.
“It’s kind of like all the stars aligned to do it, and we traded our hobby for our job and our job for our hobby,” Simpkins said.
Aged in the Tar Heel State
Although they were not raised in the Charlotte region, Simpkins and Bogan consider themselves “North Carolina guys.” Bogan, a self-proclaimed U.S. Army “military brat,” was a general contractor in the area for many years, coming to North Carolina via UNC-Chapel Hill. Simpkins, a Nashville, Tennessee, native, was ordained as a Lutheran pastor, which brought him to the state 10 years ago.
This North Carolina identity is an important part of Oaklore’s brand when it comes to business and charity, such as a $50,000 donation to the Community Foundation of Henderson County for Hurricane Helene relief, and assistance to other local charities.
A taste of NC
Oaklore Distilling came to 11136 Monroe Road in Matthews several years ago, but the work began back in 2017, with the friends spending years learning the art of distilling and crafting a signature taste at home before branching out to a larger facility.
“We are still a small business, and we still feel like a startup in a lot of ways, which is a wild process — to start something from scratch,” Simpkins said. “But we’re proud of where we are and what we’ve been able to accomplish.”
They started in a small 1,000-square-foot building in Matthews, with only 250 square feet dedicated to production. It was a challenge to make and bottle everything in such a small area.
“We were lucky to have it, and we’re thankful we knew our goal was to be a little bigger,” Bogan said.
The current facility sits on a 4-acre property, with about half of the space being used, allowing for future expansion. They also operate an outdoor area with food trucks, musicians, and amenities like an ‘80s-style slush puppy machine for children during family-friendly events.
Everything changed when Oaklore took over an old 5,000-square-foot strip mall next door for production space. The new area includes dedicated spaces for making, bottling, and storing whiskey, making their operations more efficient.
The site also features a small lab for micro-experiments on new products like bitters (rhubarb), liqueur flavors (cherry, lime, orange), and other infusions. Tom is very hands-on with production, while Simpkins handles business development, but both can step into other roles if needed.
Oaklore offers many spirits, such as its award-winning Four Grain Bourbon, which was shipped to 42 states across the U.S. this spring through its eCommerce partnership with Speakeasy/FLAVIAR.
Oaklore makes Four Grain with corn, wheat, rye, and barley, using special copper stills. They blend two types of bourbon — wheated and rye — aged separately for five to six years before being mixed together. After blending, the whiskey is aged again for eight to twelve months in North Carolina, using various barrels to create a smooth bourbon with rich, balanced flavors that aren’t too woody.
Oaklore’s Four Grain Bourbon is crafted to offer a rich flavor and a unique story. It is bottled at 92 proof and is not chill-filtered. It’s smooth enough for beginners but complex enough for whiskey lovers who want something different from the usual Kentucky bourbon. It has aromas of toasted pecans and honey cake, a taste that’s silky with toffee and vanilla, and a butterscotch finish with a touch of spice.
Other new products inside their expanded facility include an Espresso Liqueur and a new limited-edition Honey Finish product coming out soon. Oaklore uses honey from an on-site beehive to saturate the oak cask before aging the bourbon for about a year.
This popular limited release typically occurs around Black Friday, but it will be available earlier in November at the shop in Matthews.
Recent limited releases include an Oloroso Sherry Cask Finish and their popular, shop-only Bloody Butcher Corn bourbon, made from heirloom Appalachian corn. The name comes from the red corn that would stain an apron while it was being ground, making it look as if the miller were a butcher.
The business also crafts vodka, gin, and rum.
Investing in the Charlotte region
A major growth decision was acquiring a new warehouse on South Boulevard. This 50,000-square-foot space will hold all of their barrels—up to 25,000 at a time. Oaklore is also considering adding a restaurant and a vintage bourbon bar at this location.
They say they’re thinking ahead by investing in a fast, high-capacity bottling line that could help them make up to 100,000 cases a year in the future — much more than they currently produce.
Another part of their growth is a new bar and tasting room called Oaklore Bar & Bottle Shop, opening this fall in South End. Because it’s owned by the distillery, people can buy bottles there any day of the week, including Sundays.
Partnership to push Oaklore whiskey
In July, Oaklore Distilling announced a new partnership with Johnson Brothers of North Carolina, a major producer of alcoholic beverages, to support their expansion.
Johnson Brothers will direct the brand’s regional distribution strategy, according to a news release from Oaklore. The plan will focus on the Piedmont region’s humid subtropical climate, which is ideal for barrel aging, with broader temperature swings than Kentucky or other regions. This, Oaklore says, results in a more consistent, year-by-year aging process for uniform whiskey production and a richer taste.
The 72-year-old company, with operations in 17 states and more than 4,000 employees, will help push Oaklore’s whiskeys and specialty releases onto back bars and liquor shelves across the state. This will also be the foundation for a sales strategy as the company works to expand across the U.S.
Oaklore is focused on saturating ABC stores, bars, and restaurants in North Carolina and has started plans to expand into South Carolina. They use a small team of about six people for in-store tastings across the state to build brand awareness. During the fall, about 5,000 people sample their products during events, which is important for the business. After all, it’s the reason their friend Travis Master joined Oaklore as a business partner after tasting their homemade bourbon many years ago.
“People are still discovering us, and we’re at a premium price point,” Travis said. “To spend $70 to $80 on a bottle, they typically want to try it first... we make good whiskey, and we’re confident in it.”
Simpkins said starting Oaklore was like “building the plane while you’re flying it.”
They noted the challenges of staying ahead of infrastructure and supply chain needs, difficulties faced by many small business owners. They also had to deal with operating in a regulated industry, with federal laws and unique rules in each state.
When they launched their distillery, there was no established process in the area, so they had to help develop regulatory guidelines from scratch — a significant hurdle in such a tightly-controlled sector, they said.
“We’ve had to do a lot of education and work with different groups and authorities and lawmakers to help them understand what we’re doing because there’s just not a lot of precedent for it,” Simpkins said. “And distilleries are rare in a lot of ways.”
Older bourbons taste better, but it comes with a lot of work. But it’s something Oaklore embraces.
“The whiskey business is a tough business,” Bogan said about making advanced plans for future growth. “There’s not a lot of pivoting. It’s doing something that you know is really, really good and doing well for a long period of time.”
This story was originally published October 6, 2025 at 5:00 AM.
