Words by Josiah Hartline
A Cigar Bar on Wheels
For Christopher Strother, cigars have always been about slowing life down for a moment, and The Cigar Box grew from that simple idea.
If you spend enough time around events in the Upstate—concerts, golf tournaments, festivals, or community gatherings—you may notice a sleek black trailer with gold accents drawing people in for a closer look. Inside sits The Cigar Box, a mobile cigar bar that brings the experience of a cigar lounge directly to wherever people are already gathering.
The concept is straightforward but uncommon. Instead of asking people to find a cigar lounge, the lounge comes to them. At a festival, a private party, or a community event, the trailer creates a small place where people can step away from the noise, light a cigar, and relax for a while.
That slower pace is part of the appeal. Cigars have long carried the reputation of being something you don’t rush. They take time, they require patience, and they often turn a quick break into a longer conversation.
Where the Idea Began
Like many small businesses, The Cigar Box started as a simple idea built around something Chris already enjoyed.
For years cigars had been part of his routine, something he enjoyed both on his own and with friends. Eventually the thought surfaced that the hobby itself might become the foundation for a small side business.
A conversation with a friend helped push the idea forward. The friend was launching a mobile seafood operation and suggested something similar in the cigar world—a mobile cigar bar that could travel to events rather than operating out of a traditional storefront.
The first event came together quickly. Chris reached out to City Scape Winery about setting up for a Father’s Day event in 2022. When the winery asked for photos of the setup, the reality was that the setup didn’t exist yet. The business was still just an idea.
That request forced things into motion. Chris gathered cigars, created a simple display, and hosted a small launch gathering with friends to photograph the setup. Those photos went to the winery, the event was approved, and The Cigar Box had its first booking.
At the beginning, the entire operation consisted of an eight-foot folding table under a pop-up tent.
Building the Trailer
As the business began to take shape, Chris knew he wanted the presentation of The Cigar Box to reflect the atmosphere cigars are known for.
The original vision was ambitious—a fully built-out mobile cigar lounge similar to the Airstream cigar bars that exist in a few places around the country. But the cost of that type of build quickly made it unrealistic for a new business.
Instead, Chris partnered with local builder Ryan Lockwood to design something custom that would still stand out.
The result is the teardrop-style trailer that now serves as the centerpiece of The Cigar Box. Wrapped in black with subtle gold flecks, the trailer features a cedar-built display window where individual cigars are presented one by one rather than stacked in boxes.
“I wanted something that would stand out,” Chris said. “When people walk up, they’re not just seeing boxes. They’re seeing the cigars themselves.”
Inside, cedar shelving holds the cigars while velvet-lined storage keeps products from shifting while traveling between events. The trailer also includes a dedicated station for cutters and lighters, along with LED lighting that illuminates the display after dark.
Even people who don’t smoke cigars often stop to take a look.
“People come over just to see it,” Chris said. “Even if they don’t smoke cigars, they want to check it out because it’s just a cool setup.”
Making Cigars Approachable
One of Chris’s priorities has always been making the cigar experience welcoming for everyone, especially for people who are new to it.
For someone unfamiliar with cigars, the choices can feel overwhelming. There are dozens of shapes, sizes, and flavor profiles, and many people don’t know where to begin.
Chris starts by asking questions.
“People ask me all the time what my favorite cigar is,” he said. “But that doesn’t really matter because I’m not the one smoking it. They are.”
Instead of pushing his own preferences, he focuses on what the customer might enjoy. How long do they want the cigar to last? Do they prefer something mild or something with a little more strength? Are they interested in traditional cigars or something flavored?
For first-time smokers, Chris usually recommends something shorter and smoother so the experience feels comfortable rather than overwhelming.
“If they enjoy it, they’ll come back,” he said.
The Meaning Behind the Ritual
For Chris, cigars represent something deeper than the product itself.
“You can’t rush a cigar,” he said. “It’s not something you run outside and finish in five minutes.”
That slower pace is exactly the point. A cigar creates a small pocket of time where everything else can pause for a while.
Sometimes that means sitting alone with a book or a podcast. Other times it means sharing the moment with friends—talking, laughing, and enjoying the evening together.
Cigars live comfortably in both worlds. They can be a quiet personal ritual or a shared experience among friends.
Where the Business Stands Today
Today The Cigar Box travels throughout the Upstate serving festivals, concerts, corporate events, and private gatherings.
The business follows a natural seasonal rhythm. Spring begins to bring activity, summer builds momentum, and fall becomes the busiest time of year as festivals and outdoor events fill the calendar.
Because the business is mobile, it also provides flexibility that a traditional storefront wouldn’t allow.
That flexibility has become especially important recently. After Chris’s wife suffered a stroke, he stepped into the role of her primary caregiver. The structure of the business allows him to continue working while still being present at home when needed.
When an event is finished, the trailer simply returns home to the garage until the next one.
Sunday Afternoon Smokes
Alongside The Cigar Box, Chris recently launched a podcast that expands the same spirit of conversation and community.
The show, called Sunday Afternoon Smokes, began in late 2024 as a way to sit down with local entrepreneurs and professionals from around the Upstate. The format is simple: share a cigar, talk about the cigar for a moment, and then dive into the guest’s work and the story behind their business.
In many ways the podcast mirrors the same experience Chris creates with the trailer itself. A cigar naturally slows the pace of conversation, giving people time to talk more openly about their work, their path, and the lessons they’ve learned along the way.
Chris says he’d love to see the podcast grow, but growth isn’t the reason he started it.
“I do it because I enjoy doing it,” he said.
Like The Cigar Box itself, the podcast is built around the idea that good conversations tend to happen when people slow down long enough to have them.
How Chris Defines Success
For Chris, the success of The Cigar Box was never meant to be measured by the size of the business.
Running events, building the trailer, and traveling around the Upstate with cigars has been rewarding work, but Chris sees the business as only one piece of a much larger life. When he talks about success, the conversation quickly shifts away from money or growth and toward something far more personal.
“My life isn’t measured by the cigar box,” he said. “It’s measured by my relationships.”
For Chris, that means his marriage, his children, his parents, and the small circle of close friends who truly know him. Those relationships are the foundation he measures everything else against. If those things are strong, the rest of life tends to fall into place.
Faith also plays a role in that perspective. Chris is open about the fact that his outlook on life and business is shaped by Christian principles, particularly the idea that character matters more than status or financial success. The goal, as he sees it, is to live well, treat people with kindness, and take responsibility for the life you’ve been given.
“There are plenty of people in this world with more money than they know what to do with,” he said. “But they’re miserable. That’s not success.”
In the end, The Cigar Box reflects that philosophy. It’s a business built around something Chris genuinely enjoys, but more importantly it creates moments where people can slow down, connect with each other, and step away from the pace of everyday life for a while.
And for Chris, those moments—shared over a cigar and a conversation—are exactly the point
Learn More
To learn more about The Cigar Box or book the mobile cigar bar for an event, visit their website or follow along on social media. You can also listen to Christopher Strother’s podcast, Sunday Afternoon Smokes, where he sits down with local entrepreneurs from around the Upstate for conversations over a good cigar.
