One of the best road trips I’ve ever taken in North America was with my brother Jim in Mississippi. Starting in Jackson, we headed to Tupelo to visit the small birthplace shack of Elvis Presley. Follow Route 278 west and an hour later, you arrive at the home of writer William Faulkner and the attractive University of Mississippi campus in Oxford.
Continue to follow Route 278 west for a little more than an hour to reach the birthplace of the Blues, Clarksdale. The amount of musical talent that began their careers in this small town of 21,000 is remarkable. Muddy Waters was raised on the Stovall Plantation outside of town. Soul man Sam Cooke was born here, along with electric blues master John Lee Hooker, W.C. Handy, and Ike Turner, whose green house still stands on Washington Street. At the crossroads of Highway 61 and 49, early 20th-centruy bluesman Robert Johnson supposedly sold his soul to the devil in exchange for a guitar. Muddy Water’s cabin is one of the highlights of the Delta Blues Museum, housed in a renovated freight depot.
Jim and I spent two nights at one of the most unique accommodations in the country, the Shack Up Inn. Set on the Hopson Plantation, where the mechanical cotton picker made its debut in 1941, owner Bill Talbot has converted six former sharecropper shacks into his own version of a B&B (bed and beer). Each rambling shack pays tribute to a blues legend, like the one we stayed in dedicated to boogie-woogie pianist Pinetop Perkins, who once worked at this same plantation.
Head south on Highway 61 through the heart of the Delta and you’ll find the zig-zag shaped trenches Union and Confederate troops dug during the Civil War’s bloody Siege of Vicksburg, now a National Military Park. Another hour of driving and you’ll reach that gem on the Mississippi River, Natchez. During its heyday prior to the Civil War, when cotton was king, Natchez had more millionaires per capita than any other city in the country. They built palatial estates that were largely spared during the Civil War due to its proximity to Vicksburg. The Union soldiers that survived that battle and made it to Natchez burned the cotton fields but left the homes intact. More than 150 of these structures still stand, including many that are still in private hands.
That includes the Monmouth Plantation, where mint juleps are served in a frosty silver cup promptly at 6:30 in the Quitman Study. Then everyone retires to the dining room, an ornate parlor adorned with long chandeliers and portraits of General John Quitman, who called Monmouth home in the 1820s. The highlight of this comfortable retreat, however, is the meticulously landscaped grounds, shaded by centuries-old oaks and their thick dress of Spanish moss.
From Natchez, it’s a two-hour drive back to Jackson, where we checked out the relatively new Mississippi Museum of Art in the emerging cultural district. Then we dropped off our convertible PT Cruiser and flew home. For the perfect 4-5 night drive through the Deep South, this can’t be beat.
Still don’t have plans for New Year’s Eve? Consider a 2 or 3-night getaway with 
After dropping our bags off at our boutique hotel,