I Didn’t Expect Clarksdale to Feel Like This
- Roni Bossin
- Apr 14
- 7 min read
Updated: Apr 16
I just came back from the annual Clarksdale, Mississippi Juke Joint Festival, which took place April 8–12, 2026.
When did I even become aware that a place called Clarksdale exists? I can’t say for sure, but most likely sometime after 2017, when I became a tour guide in New Orleans. After that, I occasionally received requests from travelers wanting an itinerary to or from New Orleans that included historical musical stops. So at that point, all I really knew was “Birthplace of the Blues,” Ground Zero, Morgan Freeman… and that was about it.
Fast forward to 2025: I got a request to plan and guide a private tour from Nashville to New Orleans that will take place later in 2026. Since then, I’ve been preparing and scouting some of the places we’ll visit. I went to Nashville back in January and combined it with seeing a good friend who was there for work. Clarksdale, naturally, was on my list, but I hadn’t yet found a real “excuse” to go.
Then, several months back, a group of Israeli travelers who were planning to visit New Orleans mentioned that after their time in the city, they were going to attend the Clarksdale Juke Joint Festival in early April.
“Interesting,” I thought. I wasn’t even sure what that meant. In my mind, I imagined some kind of bar crawl between places with jukeboxes. It didn’t sound particularly compelling—maybe just a cute little town festival. But juke joints are something else entirely. Today, they are places where you can let loose and experience the Mississippi Delta blues the way it’s meant to be enjoyed—live, up close, informal, and full of energy. And Clarksdale has some of the best.
As it turned out, those travelers never made it—war broke out in the Middle East, and they couldn’t leave the country. I refunded their deposit, which was of course disappointing, but insignificant compared to everything else going on. Still, I found myself curious about this festival they had planned to attend.
A couple of weeks before the festival, I tentatively marked my calendar and told myself I would go if nothing major came up in New Orleans. The night before it began, I was still debating. Then I just thought—what the heck. Get in the car. Sleep in it if needed. If it doesn’t feel right, turn around.
So that’s what I did.
On Thursday, April 8, I set out early and started driving my van toward Clarksdale. Along the way, besides listening to music and chatting about life decisions with ChatGPT, I called my parents. They were in Israel, in the middle of a fragile ceasefire, and I wanted to tell them what I was up to and ask what they remembered from their own trip through this region back in 2018.
It turns out that when they were in Clarksdale, they met an older Jewish man named Floyd Shankerman, who ran a clothing store called—appropriately—Shankerman’s. They said he played music (the blues, I think) and was quite a character. They weren’t even sure he was still alive, since he had already been quite old back then.
Naturally, I was curious—especially since I give tours about Jewish history in New Orleans and the South. Google Maps listed the store as “temporarily closed,” so I wasn’t too hopeful, but I figured I’d check anyway.
After almost six hours of driving, I arrived in Clarksdale… or at least I thought I did.
I let Waze take me to “Clarksdale” without a specific destination, and the first streets and buildings I saw were not exactly in great shape. I kept driving and eventually reached the Clarksdale Visitors Center. Right next door was the Dutch Oven, where I decided to grab something to eat.
It felt like stepping back in time. The closest comparison I could think of was a scene from Witness with Harrison Ford—though I wasn’t expecting to see Amish people in Mississippi. The place is amazing. I went back the next day for breakfast—and pie. Actually, two kinds of pie. The staff were welcoming but direct—no unnecessary politeness, just genuine care for feeding people. Exactly my style.
The visitors center was closed, so I started walking around, still unsure whether this spontaneous trip had been a good idea. I didn’t really know where to begin, so I decided to check out Shankerman’s.
As I walked toward the shop, I noticed that nothing around me suggested a festival was happening. I started to feel that creeping doubt again—what did I just do?
Then I saw the big red letters: “Shankerman’s.”
The store was still there. And it was open.
Inside, it was no longer a clothing shop, but rather a very eclectic antique store filled with just about everything you could imagine. The people there were incredibly kind, and when I asked about Floyd, they immediately knew who I meant. He was still alive, but no longer running the store.
They told me that when he owned it, he would also host small music performances for visitors. Later, I learned that this kind of thing is not unusual in Clarksdale—there was even a barbershop where the barber would cut your hair and play music at the same time. Apparently, Shankerman had also been a star baseball player in college—something that caught my attention from a “previous life” of mine.
I had found my first “anchor” in Clarksdale, but I still didn’t quite know what this place was about.
When I asked what I should do next, they pointed me toward Cat Head record shop.
And that’s where things really began.
I walked into Cat Head and met a photographer named Adam David, who was signing copies of his book about Memphis and Clarksdale blues. I asked him what I should read to learn more about the music. He immediately introduced me to Roger Stolle, the owner of the shop and co-founder of the festival.
Roger started showing me books—his own included—and talking about the history of the blues. He even knew about the Israeli group that had to cancel because of the war and was genuinely disappointed for them.
You could tell how much he cares about Clarksdale.
It turns out Roger moved there in his mid-30s after a successful career in advertising. Something in him pulled him toward preserving and documenting blues music at its source—the Mississippi Delta.
It reminded me of my own decision to leave a secure job in Israel and become a tour guide in New Orleans, around the same age, also on a bit of a whim.
Maybe we both stood at a kind of crossroads.
What happened next is hard to describe.
Some people might call it “flow.”
I just followed where my feet took me—setting up a beach chair near an outdoor stage by the local brewery, Red Panther, and taking in the opening show. I honestly don’t remember who was performing.
But I remember the feeling.
There was something in the air—a shared sense of appreciation for what was happening, something simple but deeply satisfying.
At one point, the organizers gave awards to festival visitors. One American woman said Clarksdale gave her and her husband “all the spiritual nourishment they needed.” A visitor from the UK called it his “home away from home.”
I realized I had stepped into a community I didn’t even know existed—and somehow felt at home in it.
As I sat there, I noticed that most of the people around me were closer to my parents’ age. That made sense—it was only Thursday, and the main festival day was Saturday.
Then, out of the corner of my eye, I noticed two younger guys nearby, nodding along to the music. It almost felt like they were experiencing the same realization I was—that they had stepped into a parallel world where things slow down and the only problems are the ones being sung on stage.
Little did I know—I actually knew one of them.
Later that night, I went to Ground Zero. I had sent many guests there before, and it was finally time to see it for myself.
Within minutes, I stepped outside to grab something from my car—and ran into a familiar face.
Mike. Someone I used to work out with at CrossFit in New Orleans.
Next thing I knew, we were deep in conversation at the bar, with blues music playing behind us. He told me he had discovered Clarksdale ten years earlier and had been coming back ever since.
Beginning to sound familiar?
Then I looked down at the table next to us—and saw the two younger guys from earlier.
One of them was Yoni—a friend from Israel I hadn’t seen in ten years.
We had met at Toastmasters, back when I was working on my public speaking and considering becoming a tour guide.
Now we were reconnecting in Clarksdale.
Full circle.
From that moment on, we spent most of the festival together.
They were far more knowledgeable about blues than I was, but their enthusiasm was contagious. We went from place to place—Meraki Café, Cat Head, Bluesberry Café, Red’s Juke Joint—and probably a few others I’ve already forgotten.
My contribution was suggesting a visit to the Delta Blues Museum, sharing a few tour guide anecdotes (hopefully entertaining), and making some food calls—like going back to the Dutch Oven, grabbing brisket at a pop-up stand, and starting the last day at the Yazoo Pass.
At Yazoo Pass, we met “Bubba” O’Keefe, the director of tourism in Clarksdale and co-founder of the festival.
When I told him I guide Israeli groups in New Orleans and beyond, he mentioned an Israeli woman who organizes blues festivals back home and has connections to Clarksdale.
At that point, it didn’t even feel surprising anymore.
Just part of the flow.
Shortly after, I had to head back to New Orleans for a tour the next morning.
But I left with something more than just memories.
Clarksdale—you were good to me.
I’ll be back.
This experience will soon become part of a larger journey I’m building from Nashville to New Orleans.
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