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Walking in Greenwood

Updated: May 24, 2023

a Mississippi freedom trail sign for bryant's grocery with overlay text reading walking in greenwood travel story

It’s easy to forget how fast things have changed in this country. A 75-year-old person has seen the end of segregation and the election of America’s first black president. Elvis-mania has come and gone, men have walked on the moon, the internet has been born, and the Chicago Cubs have won a World Series.

Sylvester Hoover has seen it all unfold from the heart of the Mississippi Delta. It may seem like a long way off from the action, but more often than not, history has come right to his doorstep in Greenwood. Sylvester has made it his life’s endeavor to share that history with the world through his tour company, Delta Blues Legends Tours.

I met Sylvester years ago, in my bachelor days when I did more travel writing around the Delta. He’s impossible to forget, and when me and the girls trekked over for a tour, he hadn’t changed much. A wiry man with a deep voice and patient demeanor, the Delta lives in him as much as he lives in it. He’s more than happy to show you around and make the Delta feel like it’s your home, too.

Baptist Town

Near downtown but on the other side of the railroad tracks, Baptist Town is the first stop on the tour. Back in the day, Greenwood’s black residents were restricted from living in other parts of town. Sylvester operates a small convenience store there, right next to his Back in the Day museum.

The Back in the Day museum holds artifacts from, well, back in the day. From a wood-burning stove to equipment used to pick cotton and religious memorabilia, folks left these items behind or donated them over the decades as they moved away seeking better opportunity and escape from racial Jim Crow violence. With them, Sylvester paints a powerful picture of what life was like back then.

Sylvester takes guests on a walk through the neighborhood and points out places where Robert Johnson and Honeyboy Edwards lived and played. He recounts the legend of Robert Johnson’s deal with the devil. The story is fascinating and downright creepy. If you ask him if he believes it, Sylvester will tell you it’s more likely Robert Johnson was good at branding himself. But that’s not a “no,” is it?

Baptist Town, and the larger Greenwood area, served as the setting for the 2011 movie, “The Help.” If you enjoyed the movie, you’ll appreciate seeing it firsthand. Sylvester served as a location scout for the film, and he’ll give you the inside skinny on Hollywood’s depiction of the Delta.

A Mississippi Freedom Trail sign about the Black Power speech

Civil Rights sites

It’s true. In 1966, a coalition of civil rights activists including Martin Luther King Jr., Stokely Carmichael, and James Meridith marched over 200 miles from Memphis to Jackson to advocate for voting rights. When the March Against Fear passed through Greenwood, Carmichael was briefly arrested. He was released the next day and held a rally in a public park, where he first uttered the phrase.

That park is just one of many world-changing stops on Sylvester’s tour. He takes you back in time to when Greenwood’s main drag was split into a black side and a white side, and how Greenwood used to be a mecca for black commerce and, of course, music and good timin’. The road that runs along the river at the edge of downtown is still cobblestoned, from when the barges used to load up with cotton there, back when “cotton was king.”

Sylvester’s tour extends out of town a short ways to Bryant’s Grocery, the store where Emmett Till allegedly whistled at Carolyn Bryant. Unlike many historical landmarks in Greenwood and the Delta, Bryant’s Grocery has fallen into tragic neglect and disrepair. Fallen in and overgrown with vegetation, the store is barely visible, let alone recognizable. But once you’re out of Sylvester’s van and looking up at it, the gravity of it is tangible, especially as Sylvester recounts his memories of visiting the store as a boy. It’s a sight everyone — everyone — should see and feel.

a headstone for Robert Johnson

Robert Johnson’s grave and other Mississippi Delta Blues must-sees

There are several places where Robert Johnson is rumored to be buried, allegedly to throw off the devil, but Sylvester knows his true resting place. You’ll see the grave near the church where Robert Johnson died of poisoning, where musicians and poets, students and daredevils, still leave keepsakes on his headstone.

Sylvester’s tour makes a stop at the Tallahatchie bridge, of Bobby Jo Gentry fame.

The tour ends where it begins: Downtown outside the delicious Crystal Grill, where we feasted and recapped over plates of fried catfish and pie with three-inch high meringue.

Wanna go?

  • Tours are riding and walking, so dress comfortably, you’ll walk a few blocks at a time.

  • Tours are by appointment, and you can set one up by calling Sylvester at (662) 392-5370. It may feel odd to give him a call out of the blue, but just go for it!

  • Tours are $75 per person, and it’s cash only, so hit the ATM before you meet up with him.

  • The tour can accommodate 8-10 people, though if your party is larger, Sylvester may have an answer for that. He frequently gives tours to church groups and other larger parties.

Other things to do in Greenwood

Viking Cooking School

Right in downtown Greenwood, the Viking Cooking School is a great place to spend an afternoon! You can sign up for classes themed around “The Help,” a lavish dinner party, a date night, etc. I can personally vouch for the “Help”-themed class.

Turnrow Books

You probably already know that we are suckers for a good bookstore, and Turnrow is one of our favorites. The space is so clean and calm, and you can find a curated selection of cool titles and regional authors.

The Museum of the Mississippi Delta

A perfect piggyback to the Delta Blues Legends tour, the Museum of the Mississippi Delta features exhibits on art, agriculture, the Civil War, and Southern culture. Definitely worth a stop! Learn more here.

A sign attached to a building that reads Crystal Cafe Grill Air Conditioned

Dining and accommodations in Greenwood

The Alluvian Known far and wide as a luxury destination, the Alluvian hotel boasts a 7,000-square-foot spa and a historic highly-rated Italian restaurant, Giardina’s. We haven’t eaten there, but have heard good things; however, we can attest that the cocktails at the Alluvian’s bar are mighty tasty. Learn more here The Crystal Grill A Greenwood staple, the Crystal Grill sits right on the downtown railroad track and serves up Delta favorites like gumbo, fried catfish, fried chicken, steaks — the list goes on. Every time we go, I say I’m going to try something new, but end up getting the catfish anyway. And those pies, my lord. Feast your eyes here Fan and Johnny’s For slightly upscale Southern, Fan and Johnny’s offers regional favorites like fried green tomatoes, alligator bites, poboys, pimento cheese, and even frog legs. They also offer main courses like chicken parmesan and scallop Rockefeller. Learn more here Drake’s A barbecue stand set up in the parking lot of a small shopping center, Drake’s barbecue is slap-your-mamma good. See it for yourself

Who is this trip for?

Personally, I think everyone in America should take Sylvester’s tour, but for these types, the Delta Blues Legends Tour will be a slam dunk.

  • Anyone interested in Southern or American history. Sylvester is such a magnificent storyteller who can really tie the history, music, and Civil Rights all together.

  • Folks with a deeper appreciation for music. After all, the Mississippi Delta Blues are the bedrock for practically every strain of music out there today.

  • Small groups. Church groups, book clubs, girls’ trips — the cooking school, the Delta Blues Legends Tour, and other activities are memories made for a group.

  • A family trip with teenagers. If you want an educational trip that isn’t a museum, the Delta Blues Legends Tour is perfect. We took ours and the tour was great at bringing to life the bigger themes she’d heard in class.

  • The “Southern-curious.” The South has its own unique flavor, and that’s most true in Mississippi. If you’re intrigued by the South, the Mississippi Delta is a one-of-a-kind place that simply must be experienced.

Looking to explore more of The Delta? Read Alyssa’s Memphis to New Orleans: A Music Lover’s Road Trip guide over on Fora.


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