Mississippi’s oldest cigar shop expands in JXN

[JohnS]

Mississippi’s oldest cigar shop expands in JXN

By Holly Emery - Published: Aug. 25, 2025

Mississippi’s oldest cigar shop expands in JXN © WLBT

JACKSON, Miss. (WLBT) - After 55 years in business, the state’s oldest cigar and pipe tobacco store is expanding and they’re staying in the capital city. 

The Country Squire has sat in The Quarter on Lakeland Drive in Jackson for over five decades, offering both a unique and old-school style lounge for customers to shop from world-class tobacconists.

“We’ve been here through a lot of historic events. Folks have told me in the past that they watched Secretariat win the Triple Crown when they were standing at the Country Squire. Or, you know, when Willie Morris wrote ‘My Dog Skip’, he came here to sign, you know, hand out signed copies,” shop owner and tobacconist Jon David Cole said.

While the 1,500 square foot building has hosted thousands of customers from around the world, Cole is expanding the legacy business to the old Bonsai building, less than half a mile away.

The new location is more than three times the size of the current location, 5,300 square feet.

“We need more room for cigars and pipe tobaccos, and lounge space. We’re also planning on opening a cocktail lounge. Our humidor will be the largest in the city of Jackson by far. You know. We’ll have much more room to spread the covered patio outside. That’ll be comfortable for all seasons,” Cole explained.

The current location is known to be packed each weekend with regulars and those looking to just get into the hobby.

“If you’ve ever seen the show ‘Cheers’, it’s just like that. I mean, you walk in and everybody knows who you are. It’s family, really. And sometimes you want to get here early to get a good spot because it’s going to fill up quick,” Lee Stringer, a customer of the shop since 2019, explained.

“When they moved into here, in a matter of weeks or months, it was busting at the seams. They just need more space,” second-generation customer Mike Armstrong said.

While space was available in other cities, Cole said staying in Jackson was the goal.

But with more than five decades of history packed into the little shop, customers hope the new location will feature the same unique, old-school, lounge environment and community.

“A lot of people come because it’s something new, kind of like a restaurant. The difference is, when the newness of a restaurant is worn off, they go somewhere else. The newness of the new store will not wear off; it’ll just bring more and more people and make you want to come back,” Larry Nesbit, a customer for 53 years, said.

“There’s fancy, glitzy cigar shops all over the country, and we’re a little different, you know, so we’re going to upgrade our amenities, upgrade our stature a little bit, but we want to stay the same Country Squire. That’s really important to our vision and our DNA,” Cole said.

Cole believes the new location will be ready for customers by Christmas... and plans to host a grand opening party in January.

Source: https://www.wlbt.com/2025/08/24/mississippis-oldest-cigar-shop-expands-jxn/