Vicksburg stands on high bluffs above the Mississippi, and in 1863 that height made it the most important place in the western theatre of the American Civil War. Abraham Lincoln called it the key: whoever held these bluffs controlled the river. Ulysses S. Grant spent months trying to take it, then besieged the city for forty-seven days until the Confederate garrison surrendered on 4 July 1863. Together with Gettysburg the day before, it turned the war, and the town famously did not celebrate the Fourth of July for many decades afterward.
The Vicksburg National Military Park wraps around the east and north of the city, and its tour road of about sixteen miles is one of the most rewarding slow rides you can do in the South. It winds over the old earthworks, through ravines and past more than a thousand monuments and markers, many of them elaborate state memorials in marble and bronze. Near the end you reach the USS Cairo, a Union ironclad sunk by a mine in the Yazoo River in 1862 and raised a century later, now displayed under a canopy beside a small museum. Take the loop at a walking pace, which is what it deserves, and watch for cyclists and runners.
There is another surprise in town. In 1894 a local candy merchant, Joseph Biedenharn, became the first person to bottle Coca-Cola, so it could be sold beyond the soda fountain. His shop is now a small museum on Washington Street. Downtown also has painted floodwall murals and a riverfront where the water is not quite the Mississippi: the river changed course in 1876 and left the city stranded, and engineers later diverted the Yazoo River into the old channel to give Vicksburg its waterfront back.
For the Great River Road, this is a natural overnight. The city has every service, from fuel and repair shops to good Southern cooking, and casinos along the river if that is your thing. The roads north into the Delta are flat and straight, while those south toward Natchez roll through wooded loess hills with deep cuttings where the soft yellow soil stands in vertical walls. Summer heat is serious, so start the battlefield loop early in the day.