The Ultimate Mississippi Road Trip

Celebrate legendary musicians, literary giants, and civil rights pioneers on a scenic capital-to-the-coast loop through Mississippi. The roughly 800-mile route begins and ends in Jackson, leads through rural areas and college towns, and includes stops on the Mississippi Blues Trail.

Jackson

Mississippi’s capital and largest city boasts two new (open December 2017) state-of-the-art museums: the Mississippi Civil Rights Museum and the neighboring Museum of Mississippi History (both closed Mondays). Galleries are packed with highly interactive exhibits (linger in the Civil Rights Museum’s “This Little Light of Mine” central gallery to get the full effect), so spend a few hours at each museum. Break for lunch at Preserve, the new (open December 2017) farm-to-table restaurant inside the Mississippi Museum of Art (closed Mondays). Through July 2018, check out the museum’s special Mississippi bicentennial exhibitions. Continue the afternoon’s artsy theme in Fondren, the historic-hip neighborhood located a 10-minute drive north of downtown. End the day on a quintessentially Mississippi note by listening to live blues (Thursdays to Saturdays) at Underground 119. Or, see who’s playing at Hal and Mal’s.

Eat and Stay: Brent’s Drugs and Old Capitol Inn

Indianola/Greenville/Cleveland

Crank up the blues for the 95-mile drive north (via U.S. 49) from Jackson to the Mississippi Delta. Learn about the region’s deep musical roots in Indianola at the B.B. King Museum and Delta Interpretive Center (closed Mondays November to March). Listening stations and other interactive exhibits tell the story of the late blues icon B.B. King, who is buried on the museum grounds. A 35-minute drive north (via MS 448 and U.S. 278) is the new (opened 2016) GRAMMY Museum® Mississippi in Cleveland. Write, record, and mix an original blues song in the museum’s interactive pods. Visit the Mississippi Gallery to learn about homegrown music legends like Leontyne Price. Before leaving town, make a pilgrimage to historic Dockery Farms, the former cotton plantation known as “the birthplace of the blues” (and a stop on the Mississippi Blues Trail). For supper, drive 40 miles southwest (via U.S. 278) to Greenville for beef tamales at the original Doe’s Eat Place (closed Sundays) on the Mississippi Delta Hot Tamale Trail.

Eat and Stay: Doe’s Eat Place, Greenville, and the Thompson House, Leland

Oxford/Tupelo

From Greenville, take U.S. 278 north 73 miles to Clarksdale and the Delta Blues Museum (closed Sundays). Tour the museum and take the requisite Instagram pic of Clarksdale’s famous “Devil’s Crossroads” sign (three blue guitars marking the intersection of U.S. 61 and U.S. 49). Continue east on U.S. 278/MS 6 for 63 miles to Oxford. Considered a literary hub—famous writers with ties to the town include William Faulkner and John Grisham—Oxford is home to the University of Mississippi. Visit the University Museum (closed Sundays and Mondays). Walk the adjacent Bailey’s Woods Trail to tour Faulkner’s home, Rowan Oak (closed Mondays). Stock up on road trip reads at independent Square Books on Oxford’s historic town square. Drive east on U.S. 278 for 55 miles to Tupelo, headquarters of the Natchez Trace Parkway. Celebrate Tupelo’s favorite son at the Elvis Presley Birthplace. See over a hundred vintage cars at the Tupelo Automobile Museum. Stop by the Blue Canoe juke joint for live music, burgers, beer (32 on draft), and to-die-for bread pudding made with blueberry doughnuts from local favorite Connie's Fried Chicken.

Eat and Stay: Harvey’s and Moon Lake Farm, Belden

Columbus/Meridian

Follow ALT 45 to U.S. 45 for the 145-mile drive south to Meridian. Or, if time allows, take a scenic detour on the Natchez Trace Parkway. Enter the parkway in Tupelo (Mile Marker 256) and exit at U.S. 82 (Mile Marker 204). From there, follow U.S. 82 east 42 miles to hop on ALT 45 south in Columbus, home to more than 20 National Register of Historic Places properties. Tour the Tennessee Williams Home and Welcome Center (closed Sundays) and get lunch at Huck’s Place (try the chicken and sausage gumbo). Continue south 95 miles (via U.S. 45) to Meridian. Call ahead for a guided tour of the Mississippi Industrial Heritage Museum at Soule Steam Feed Works. Take a spin on the hand-carved Dentzel menagerie carousel, operating since 1909 and open Saturday afternoons year-round (and more frequently spring to fall). For live entertainment, check the calendar at Brickhaus and Mississippi State University’s historic Riley Center.

Eat and Stay: Weidmann’s and Century House Bed and Breakfast, Meridian

Biloxi/Ocean Springs

From Meridian, follow I-59 south about 90 miles to Hattiesburg. Stop for lunch at Cotton Blues (try the BBQ pulled pork fries) before heading south (via U.S. 49 to MS 67) 74 miles to Biloxi. Spend a few days exploring Biloxi, neighboring Ocean Springs, and the Mississippi sections of the Gulf Islands National Seashore. Buy a Mississippi Gulf Coast Attraction Pass ($32) for onetime entry to eight top area attractions, such as the Ohr-O’Keefe Museum of Art (closed Sundays and Mondays) and the Maritime and Seafood Industry Museum (closed Sundays December to February) in Biloxi, and the Walter Anderson Museum of Art in Ocean Springs. March to October, rent a kayak, Jet Ski, or other water toy from Get Wet Beach Rentals at Biloxi Beach. Before returning to Jackson (166 miles north via U.S. 49), catch a live blues performance at the Government Street Grocery or Murky Waters in Ocean Springs.

Eat and Stay: Mary Mahoney’s Old French House, Biloxi, and The Roost, Ocean Springs

Maryellen Kennedy Duckett lives, writes, and drives the backroads in East Tennessee where she wakes up curious every day. You can follow her on Twitter @mekd.