Jerry Holt gazed at the old cotton gin at historic Dockery Farms with a bit of wonder. The massive red, rusty Murray 90 machine looked hauntingly familiar. Suddenly, memories came flooding back on this sun-dappled afternoon along the Mississippi Blues Trail.

Holt grew up here in the Mississippi Delta, chopping cotton in the mid-1970s for $7 for a 12-hour day. He recalled his older neighbor losing some fingers in an accident with a gin like the one at this plantation-turned-­museum.

“We called him Six Fingers,” Holt said, his recollection more harrowing than heartwarming.

Dockery, once a 25,000-acre plantation in Cleveland, Miss., claims to be the birthplace of the blues, because seminal bluesman Charley Patton once worked there. So, too, did Howlin’ Wolf and Pop Staples, names known to music fans.

Nearby Clarksdale, Miss., also claims to be the birthplace of the blues because, as legend has it, an ­aspiring young musician named Robert Johnson made a deal with the devil at a Clarksdale intersection to learn how to play guitar. With such songs as “Dust My Broom” and “Cross Road Blues,” Johnson is regarded as one of the most influential bluesmen of all time, thanks to his pioneering recordings from 1936 to 1938, when he died at age 27.

You can hire guides to learn the rich history of the Delta blues in Mississippi, though they may disagree on where exactly the music was born. This Minnesotan got two views of the area from two native sons: Lock Bounds, 79, my St. Paul neighbor of 22 years who grew up white and middle-­class in Clarksdale; and photographer Holt, 62, my Star Tribune colleague of 30 years who grew up Black and working-class in Boyle, a hamlet surrounded by cotton fields.

Over the course of a one-week journey back to the Delta last fall, Bounds and Holt found that things have changed, but times are still hard for Mississippians. Maybe that’s why the blues still resonates there like a black cat moan.

Blues mecca

“This is not the Clarksdale I knew,” said Bounds on a stroll through downtown, where murals of blues figures may outnumber the open businesses. He did point out Shankerman’s, where he bought a suit when he went off to college. Now the grandson of the original owner runs the 104-year-old menswear shop.

The red-brick Hotel Alcazar, where a young Ike Turner worked as a janitor and elevator operator, stands vacant, begging for tenants like so many other buildings downtown.

Another landmark lodging, the Riverside Hotel, where Black entertainers like Sonny Boy Williamson stayed in the segregated South, fell victim to a violent rainstorm a couple of years ago. Formerly the G.T. Thomas Hospital in which blues star Bessie Smith died in 1937, the sprawling, downtrodden Riverside has a GoFundMe campaign to spur its rehabilitation.

Despite being as down on its luck as a blues lament, Clarksdale, population 14,000, remains a mecca for music lovers. They make the pilgrimage to “The Crossroads,” the historic Robert Johnson site marked by a signpost at the intersection of Old Hwy. 61 and Old Hwy. 49. The site is next to Abe’s BBQ, open since 1924.

Not all of Clarksdale appreciated its musical roots. “The blues didn’t affect us; we lived on the other side of town,” said Bounds, who left Mississippi in 1970 but would return occasionally to see his mother and lunch at Abe’s.

But blues-loving rock stars certainly know Clarksdale. Jimmy Page and Robert Plant titled their 1998 album “Walking Into Clarksdale,” and since 1999, Eric Clapton has organized the periodic Crossroads Guitar Festival in various cities.

Today, blues devotees head to Clarksdale’s aptly named Ground Zero, a spacious memorabilia-filled live blues emporium co-owned by actor Morgan Freeman. His affiliation certainly boosts the appeal of this touristy restaurant/nightclub (capacity 1,200) in what was once a wholesale grocery. There are rooms to rent upstairs.

By contrast, Red’s Lounge, a genuine juke joint, has served up a true taste of the blues for four decades. With room for maybe 70 people, Red’s is a no-frills, cash-only dive bar that doesn’t even have a stage, just a space for musicians and their equipment.

Several well-known musicians — blues and otherwise — were born in Clarksdale. Exhibits about natives John Lee Hooker, Sam Cooke, Son House and Ike Turner are showcased at the Delta Blues Museum, housed in an old railroad depot. Also featured are the 1939 Ford Tudor and recording gear in its trunk that Alan Lomax used to make historic blues field recordings, as well as a priceless Muddy Waters relic — the frame of the resurrected cabin he lived in from 1915 to 1938.

While the Delta Blues Museum explores the past, the Cat Head is the one-stop shop to learn about what’s going on now. Affable proprietor Roger Stolle, who moved to Mississippi in 2002, is a scholar, DJ, collector, author, advocate and unofficial chamber of commerce, whether for restaurant recommendations or driving directions down the Blues Trail. He sells recordings, books and regional folk art.

Bounds, my guide, has deeper Clarksdale roots. As we drove around his childhood neighborhood, he shared the local lore about playwright Tennessee Williams, who lived there from 1917-32. Bounds explained that Baby Doll Peacock, sister of Williams’ pal Eddie, sparked the name of the title character in the Williams-­penned movie “Baby Doll,” while Miss Annie Cage’s boardinghouse on Catalpa Street had a glass menagerie that inspired the Williams play.

‘The Ritz we ain’t’

Bounds recommended the Shack Up Inn as the place to stay in Clarksdale. With the slogan “The Ritz we ain’t,” this idiosyncratic motel offers updated shotgun shacks from Southern plantations, each with a bluesy moniker such as Cadillac or Hoochie Coochie. Some have televisions; all have air conditioning, bathrooms, vintage furnishings and determinedly rustic vibes.

“This is nicer than my house growing up,” said my colleague Holt of the cozy cabin he stayed in, dubbed Biscuit.

However, that night, Holt sat under the tin roof reflecting on his life, feeling uncomfortable in a commercialized plantation-like venture.

“You don’t want to make a mockery of how you grew up,” said Holt, whose parents kept him away from blues music because it spelled trouble to them. “I know what the struggle was. That is the whole experience of why you sing blues music.”

He’s glad he stayed at the Shack Up Inn, though. “I’m not sure I would endorse it. This may sound racist, but I don’t mean it to be: But if the owners were Black, I might feel differently.”

Bill Talbot, a jovial, quick-witted man with bushy sideburns, runs the Shack Up Inn, which opened in the mid-1990s. “Sixty percent of our visitors are from out of the country,” he told us. During our stay, we encountered people from Australia, Germany, Canada and various states.

Talbot pointed out that 13 small blues festivals — chiefly in the spring and fall — are key attractions for Clarksdale.

One of the biggest music events in the area is the King Biscuit Blues Festival, just across the Mississippi River in Helena, Ark. The annual festival is held the weekend before Columbus Day.

On the Blues Trail

Throughout Mississippi, posted signs at historic spots designate either the Blues Trail or the Freedom Trail.

Greenwood has a nod to Bobbie Gentry, who lived there and famously sang “Ode to Billie Joe.” The ­Tallahatchie Bridge depicted in her pop hit collapsed in 1972, but a new one salutes her. Down the road is the long-closed Bryant Grocery, where Emmett Till, a Black teen visiting from Chicago in 1955, was accused of whistling at a white woman; the accusation led to his lynching.

Midway between the bridge and the grocery is Johnson’s grave. There are three gravesites for him in the area, but the one next to the white clapboard Little Zion Church (services only on the third Sunday of the month) was deemed official in 2000 by a woman who saw her husband dig the grave. It has all the earmarks of a pilgrimage site, with people leaving coins, plastic flowers, guitar picks and other trinkets.

Other noteworthy stops on the Blues Trail provide a contrast between the academic and the authentic. Opened in 2008 in Indianola, the $15 million B.B. King Museum & Delta Interpretive Center offers a thorough multimedia look at King’s rise from farm boy to radio DJ to blues icon, with plenty of filmed interviews. On display are everything from mysterious tonics for which he sang radio jingles to his last two guitars named Lucille and his Champagne-­colored Rolls-Royce.

The Blue Front Cafe in Bentonia is the blues that time forgot. The area’s oldest surviving juke joint is run by musician Jimmy “Duck” Holmes, whose parents opened the place in 1948 to feed sharecroppers. The walls are covered with faded posters, unframed photos, various guitars and a modern cooler full of soda. If you’re lucky, the cinderblock structure will be open, and Holmes, 75, a first-time Grammy nominee four years ago, will grab one of his guitars and share some haunting Bentonian blues. Call ahead before making the drive.

In his hometown of Boyle, Holt drove us past two or three juke joints from his youth that have long since been shuttered. Things have changed here. Teenagers in Boyle now attend high school in neighboring Cleveland. Holt was stunned by the new Lyric Hotel — swanky for Cleveland but maybe 3.5 stars in Memphis two hours away. It’s just down the street from Delta State University and the modern Grammy Museum, which opened in 2016.

Witnessing the newness and oldness of his home state was emotional for Holt, who still has relatives and friends in the Delta.

“I’m still not proud of the state, to be honest,” he said.

“But I’m really proud of the people who have figured out how to navigate it and survive and excel at whatever they’re doing.”