Festival from Kansas City lounge hopes to showcase a scene ‘on the rise’
Sherri’s Executive Lounge is preparing to bring back its Cigar Festival for a second year, returning with a larger lineup and a broader pitch for what cigar culture can look like in Kansas City.
The two-day event, also called the Kansas City Culture Festival, is scheduled for May 29 and 30 under the historic Jefferson Bridge, 2130 Jefferson St. Organizers plan to fill the bridge with live music, cigar vendors, food trucks, artists, boxing and after-parties.
For owners Jason and Nayeli Sharp, the festival is built not only for seasoned cigar smokers. It is an extension of the lounge they have created on Genessee Street, a place centered on conversation, live music and a slower pace than the club scene. The bridge event is meant to take that same atmosphere into a larger public setting while tying cigars to Kansas City’s music, arts and small-business communities.
“We wanted to bridge the cultures that exist within Kansas City’s walls and beyond,” Jason Sharp said. “We really wanted to have a space that was inviting and welcoming. It was a grown folk space that we could share and influence the ideas that we had in terms of how we manage nightlife in Kansas City.”
The festival’s first year gave the Sharps a test run. Sharp and his wife said last year’s event drew about 3,000 people over two days, with visitors coming not only from the metro but from about 10 states. He described the first year as turbulent but successful, shaped by the usual challenges of permits, logistics and public skepticism, but also by the sense that there was room for a festival built around cigars, jazz and community.
That first turnout also gave the Sharps evidence that the audience for cigar culture in Kansas City extends beyond lounge regulars. Sharp saw one of the biggest early hurdles was getting people to move past the assumption that a cigar-and-jazz crowd would bring problems. Instead, he said, the event showed that a large public gathering could still feel orderly, adult and community-minded.
This year, organizers are leaning further into that crossover appeal. Along with cigars, the festival will feature boxing on Saturday night, local artists, food vendors, and new VIP drinks and tastings. The added tastings are part of an effort to make the event feel wider than a smoker-only gathering and give more guests a reason to show up under the bridge.
“We’re trying to draw people from a music perspective and then we introduce them,” he said. “We’re trying to draw people from an art perspective and then we introduce. Cigars are generally associated with whiskey and bourbon. Well, we’re going to have beer at the festival this year and there’s a lot of beer drinkers that don’t necessarily associate that with cigars.”
That broader approach is central to how the Sharps say they are helping shape cigar culture in Kansas City. They describe the local scene as close-knit but growing, with lounges, blenders and businesses often collaborating even while operating in the same market.
It also gives local cigar brands a public stage. Among the local vendors expected at this year’s festival are Emami Cigars out of Lawrence, Bad Ash Cigars out of St. Joseph and Bautizado en Fuego out of Kansas City. By placing those brands at the center of the weekend, the Sharps are using the event to show that the metro’s cigar identity is not just imported from somewhere else, but is being built locally through small blenders and boutique brands.
That visibility matters to vendors like Robert Rodriguez, owner of Chi State of Mind Cigars, who will return to the festival this year. Rodriguez moved to Kansas City from Chicago a little over two years ago after his wife received a promotion for work. He said his boutique brand had been in the works for several years, but it officially got off the ground after he moved to Kansas City. He currently sells two lines, Baptizado en Fuego and Fuego y Ceniza, both hand-rolled in Nicaragua through a small factory led by a third-generation roller.
Rodriguez said last year’s Cigar and Jazz Festival was not only his first time participating in the event, but his first event as a brand. For a newer business, he said, the festival offered a chance to be seen alongside other vendors, introduce his product to a wider crowd and begin building relationships in the local cigar market. He credited Jason Sharp with helping open those doors.
“With the local cigar scene, I would say it’s really vibrant. It’s really on the rise,” Rodriguez said. “Jason Sharp doing the cigar fest is very big for the culture and Kansas City. The more stuff like that, the more the cigar business will thrive, I would say. The more the community will come together with stuff like that.”
Rodriguez said more festivals and vendor events would help boutique cigar brands across the city by creating more opportunities to tell their story and get their product in front of people. That point aligns with what the Sharps have tried to build through the festival and through the lounge itself, where they regularly host cut-and-lights, performances and arts programming.
One of the most visible examples of that broader approach is Nayeli Sharp’s cigar line, Liga de Mujeres. The line is marketed toward women, though both owners say it appeals to a wider range of smokers. Nayeli Sharp said some of the cigars are smaller and easier to hold, while others are larger, fuller smokes that women and men both enjoy. The line pushes against the idea that women cigar smokers are looking for only one type of product.
Rather than leaning only on sweet profiles, she said the line makes room for stronger, more robust cigars as well that are not harsh or overwhelming. The women’s line becomes part of the Sharps’ larger effort to widen who is seen inside cigar culture and who feels invited into it.
Outside the festival, the Sharps have also tried to make Sherri’s a space that operates beyond nightlife. The lounge hosts monthly poetry nights, live saxophone and painting sessions, fundraisers and community discussions. Jason Sharp said the business has raised money for Ronald McDonald House, supported the I Am Down Foundation and regularly sends cigars to troops overseas through Cigars for Warriors. The lounge has also hosted civic events and conversations meant to bring together people with different perspectives.
That community service work gives the festival a larger frame. The same business using the bridge to showcase cigars, music and local vendors is also using its own space to support artists, charities and public dialogue. For the Sharp and her husband, those efforts are tied together. Both are built around the idea that a lounge can be a gathering place and that cigar culture can be connected to service, mentorship and neighborhood relationships.
“We’re trying to have something for everybody,” she said. “Not just the cigar connoisseur. The artists, the food, right? Who doesn’t love food, who doesn’t love music? If they don’t like smoke, there’s going to be other things. And then the vendors as well. There’s going to be lots of different vendors for everyone to shop locally.”
As the second festival approaches, The Sharps expect the event to continue growing. Jason Sharp believes the bridge may eventually become too small for the turnout the Sharps are trying to build, though he said he still sees it as an important cultural site for smaller events. For now, the weekend serves as both a festival and a statement about where he believes the city’s cigar scene is headed.
That future, he said, depends on continuing to create opportunities for local vendors, musicians and artists to be seen together in one place. It also depends on keeping cigar culture tied to hospitality and connection rather than limiting it to a niche audience. In that sense, the festival has become more than an annual event. It has become one of the Sharps’ clearest arguments for how the culture can grow in public.
“If we can find an opportunity to support local vendors and artists, we’re going to deploy that opportunity,” Jason Sharp said. “We deploy that opportunity here in our lounge, but elsewhere when we’re hosting events. It doesn’t matter what that event might be.”
This story was originally published April 21, 2026 at 12:53 PM.
