Trip Guide: Two Days in Cleveland, Mississippi

McCartys Pottery

Cleveland, Mississippi 

At the turn of the 20th century, workers Henry Sloan, Charley Patton, Willie Brown, Roebuck “Pops” Staples and Son House, among others, would end their day at Dockery Farms plantation outside Cleveland, Mississippi, relaxing on the steps of the commissary. Here they performed a unique sound at the time, one that would inspire many musical forms in the coming decades.

Visitors may walk through the empty buildings of today’s Dockery, arguably where the Delta blues began. It’s a major stop along Mississippi’s Blues Trail, and one that spokes out from the quaint Delta town of Cleveland.

Day One

Morning Just off the Blues Highway (U.S. Highway 61) that runs from Baton Rouge to Memphis lies Cotton Row, the historic heartbeat of Cleveland. Stroll the brick-paved sidewalks to enjoy boutique shopping, bookstores, antiques shops, restaurants and the Martin and Sue King Railroad Heritage Museum housed in the old train depot.

Lunch Enjoy Delta favorites such as hot tamales, barbecue and burgers at the laid-back landmark restaurant Airport Grocery. In addition to authentic Southern fare at this Highway 61 establishment north of downtown, visitors will find pool tables, a spacious patio and occasional live music.

Afternoon Because of the Delta’s contribution to the blues — and arguably the evolution of most modern popular music — Cleveland was chosen for the second Grammy Museum, the first being in Los Angeles. Visitors will learn about Mississippi’s contribution to America’s music through interactive exhibits on rock, hip-hop, country, R&B, jazz and more. Two temporary exhibits on display until the end of the year include “80s Rock: The Wildest Decade in Music,” which examines the rise of glam and hair metal through artifacts, multimedia displays and fan culture, and “The Killer, The Preacher and the Cowboy,” spotlighting three entertainment icons and cousins from Ferriday and Natchez: Jerry Lee Lewis, Jimmy Swaggart and Mickey Gilley.

Pop into Delta State University’s Delta Center for Culture & Learning next door, which works to educate folks on “Mississippi Delta culture and history and its significance to the world.” The campus also includes the Dave “Boo” Ferriss Museum, dedicated to the Boston Red Sox pitcher, and the Mississippi Delta Chinese Heritage Museum.

Evening Check into the Cotton House on Cotton Row, an innovative boutique hotel that honors the Delta’s culture and music with artwork and indigenous pottery. For drinks, head up to Bar Fontaine on the hotel’s top floor to sample creative cocktails and Italian-inspired small plates along with a fantastic view of town.

Grammy Museum

Day Two

Morning The New York Times and many other foodie publications have recognized Leña Pizza + Bagels as a pizza destination but every Saturday morning they serve their famous wood-fired bagels until they sell out. Come for the bagels, but return for the traditional Neapolitan pizza with locally sourced Delta ingredients —  including pecans from River Road Pecans.

Road trip Take a ride to Dockery Farms, established in 1895 as a cotton plantation but widely regarded as the birthplace of the Delta blues due to the musicians who lived, worked and played here. Mississippi is known for its unique pottery styles and Cleveland features two studios to visit: McCartys Pottery famous for its signature nutmeg glaze and distinctive Mississippi River stamp, and Peter’s Pottery in Mound Bayou that blends contemporary design with traditional Delta craftsmanship.

Leña Pizza + Bagels

Afternoon All that driving makes one thirsty. Pause at Rosedale Distilling for complimentary tours of the restored distillery and enjoy flights of bourbon, rye and the newly released Perry Martin Old Original Aged Whiskey in the tasting room. 

Evening Return downtown hungry and enjoy steaks, fresh seafood and Southern-inspired cuisine at the relaxed Backdraft Restaurant & Bar on historic Cotton Row, a short stroll from the Cotton House.

Don’t Miss

Cleveland’s annual “50 Nights of Lights” begins in early November with more than 100,000 lights throughout downtown, a community tree lighting, displays sponsored by local businesses and special events that range from live music to an arrival from Santa. The fun happens through Jan. 1, 2027. For updated information, visit 50nightsoflights.com.