New cigar shop and bar opens in downtown Louisville. What to expect...

[JohnS]

New cigar shop and bar opens in downtown Louisville. What to expect

Amanda Hancock, Louisville Courier Journal - Thu, February 12, 2026 at 9:02 PM 

When Jack and Sandra Cowley got married at the Louisville Thoroughbred Society in June 2024, with a live Cuban band in tow, the newlyweds didn't yet know they'd be opening a business next door.

“It was meant to be,” Jack Cowley told the Courier Journal.

The new business in downtown Louisville, called Havana Jack’s Cigar Factory, represents a little bit of each part of the couple.

Sandra Cowley is from Havana, Cuba. And her husband, a Louisville native, has a passion for cigars.

“She puts the Havana in Havana Jack,” Jack Cowley said.

Havana Jack's Cigar Factory, a cigar shop and bar, opened in early 2026 at 201 E Main St. A grand opening is set for Feb. 14. - Amanda Hancock, Courier Journal

While his wife owns her own business and is behind the scenes in the cigar operation, you’ll likely be greeted by Jack Cowley when walking into Havana Jack’s Cigar Factory, 201 East Main St., which opened next door to a location of Ehrler's Ice Cream in early 2026. A grand opening is planned for Feb. 14.

Donning a panama hat with four playing cards and a leaf of tobacco poking from the brim, owner Jack Cowley said this place, serving as a cigar factory, cigar shop and full bar, has been years in the making.

He first got the idea as a salesperson for the Horton Fruit Company, a local fruit and vegetable production company that employs a lot of Cuban people, according to Cowley. By befriending his coworkers and meeting his wife, Cowley’s appreciation grew for Louisville’s rising Cuban population. So did his curiosity for cigars.

Havana Jack's Cigar Factory, a cigar shop and bar, opened in early 2026 at 201 E Main St. A grand opening is set for Feb. 14. - Amanda Hancock, Courier Journal

“There is no cigar factory in all of Kentucky where they're producing hand-rolled premium cigars,” Jack Cowley said. “But we have all this talent in the Cuban community.”

He crafted a plan to open Havana Jack’s Cigar Factory, where a custom line of cigars are hand-rolled and available for sale. It helped that, in March 2025, Louisville Metro Council voted to allow people to smoke inside cigar bars.

“It’s almost kind of like when you go to a brewery and you can sit at the bar and you watch them brewing beer while you're drinking the beer,” Jack Cowley said. “It's ... hypnotizing to watch them roll cigars.”

Inside Havana Jack’s walk-in humidor, you’ll find four different cigars, each corresponding to a playing card. That includes the Jack of Hearts, a Candela cigar featuring Kentucky-grown tobacco and a green wrapper sourced from Ecuador.

“That’s most people's favorite,” Jack Cowley said, adding he expects to introduce more cigar options in the future.

Havana Jack's Cigar Factory, a cigar shop and bar, opened in early 2026 at 201 E Main St. A grand opening is set for Feb. 14. - Amanda Hancock, Courier Journal

Havana Jack’s is also outfitted with a piano area, where the duo will host live music, and a card table, complete with “Dogs Playing Poker”-inspired artwork on the walls.

The bar menu includes cocktails such as a mojito, multiple types of daiquiris, an espresso martini and a milk punch, made with bourbon, whole milk, simple syrup, vanilla extract, and a sprinkle of nutmeg. The menu also has a page of pairings, suggesting what type of drink might go well with each cigar. For example, the Jack of Diamonds, a Connecticut-style of cigar, pairs well with pilsners, rum, gin, light beers, white wines, sparkling wines, coffee, and soft-spirit cocktails “that support the light creamy notes and won’t compete with the cigar," according to the menu.

And, as a sign that Jack Cowley expects to see plenty of tourists at Havana Jack’s, a mint julep is also available year-round.

He calls the cigar shop a “natural addition” to Whiskey Row and an attraction for locals aside tourists, especially as the 152nd Kentucky Derby approaches on May 2.

“We have horse racing, we have bourbon, and now we're going to have our own hand-rolled cigars right here on Whiskey Row,” Jack Cowley said. “To me, it’s kind of like the Holy Trinity.”

Source: https://eu.courier-journal.com/story/life/food/spirits/2026/02/12/havana-jacks-cigar-factory-bar-downtown-louisville-location-opening/88219358007/