Adventure Cycling Association

We’ll initiate our 448-mile journey by meeting up in the morning in Jackson, MS, where we’ll set out on a two-hour shuttle ride to the trailhead in Natchez. Once we arrive, we’ll be free to visit the abundant sites of Natchez, established by French colonists in 1716 and capital of the Mississippi Territory until 1822. Natchez was the ultimate destination for thousands of boatmen who navigated the Mississippi River in their heavily laden flatboats and keelboats. After selling their goods and boats at market, many would return home to the Ohio River Valley by way of the Natchez Trace. After self-guided touring around Natchez as a shakedown, we will gather at 4PM in the hotel of the lobby for our orientation meeting and meal together.

If you didn’t know it already, you’ll quickly realize you’ve entered the Deep South as we begin cycling beneath a canopy of moss-draped trees lining the road. Our first day on the Trace will be an easy one, providing additional time to visit the sites of Natchez and of the Natchez Trace itself. Highlights of the latter include the sunken trace, a deeply eroded stretch of the original trail, and Emerald Mound National Historic Landmark, one of the largest Native American mounds in North America. Encompassing eight acres, Emerald Mound was built between AD 1250 and 1600 by ancestors of the Natchez tribe, who apparently used it for ceremonial purposes. Later in the day, we’ll make the side trip to Port Gibson, the town General Ulysses S. Grant said was “too beautiful to burn.” We’ll camp nearby at the Rocky Springs Campground.

The scenery continues to alternate between hardwood forest, supporting plants and trees common in the subtropics, and open pastures and cotton fields as we make our way toward, but not into, the Mississippi capital of Jackson. The Civil War left its mark on this section of the Trace, as several skirmishes occurred in the area, including the Battle of Raymond, a clash that was part of General Grant’s Vicksburg campaign. We’ll also take time to explore the Clinton Visitor Center, built with period materials and architectural details, lending it the look and feel of the farmhouses that once lined the Trace. Sit a spell in a rocking chair on the porch and relax. We will end the day at a Ridgeland hotel.

This is one of the flattest parts of the Parkway, yet the day is long and the terrain varied enough to persuade you to shift gears often enough, especially in and around the hills near our campground for the eve. Opportunities to take a break during the mega-mileage day come at the Cypress Swamp, where a boardwalk trail leads over water through a tupelo/bald cypress swamp (watch for alligators!), the French Camp Historic District log-cabin village, and the town of Kosciusko, where billionaire celebrity and philanthropist Oprah Winfrey was born.

As we head north from the campground, the Trace rolls up and down through the Red Clay Hills before settling into bottomlands near the headwaters of the Big Black River. Another pivotal battle of the Vicksburg campaign was contested near this river when Union forces under Grant defeated Confederate troops led by General John C. Pemberton. The miles just seem to zip by along this central section of the Trace with only a handful of minor hills and few changes in the uniform surroundings. The vast hardwood and pine forests that prevailed in the old days are gone, but miles and miles of mature second-growth stands line the Parkway today.

Early in the day, we’ll skirt Tupelo, the birthplace of Elvis Presley. Who knew how close we came to never enjoying the King of Rock ’n’ Roll: when Elvis was just one year old, he and his family survived a tornado that killed more than 200 of their fellow Tupelonians. Tupelo is also home to the Natchez Trace Headquarters, located adjacent to the Parkway at milepost 266. There you’ll find an information center with exhibits and a hiking trail that goes to the Old Town Overlook and Chickasaw Village Site. The rest of the day takes us through a tangle of terrain that varies from wetlands to the Tombigbee Prairie to the Appalachian foothills. The differences may be less dramatic than what you could encounter in Maine or Montana, but the observant will no doubt discern the subtle changes in flora and geography.

On this, our penultimate day of pedaling, we’ll awaken in Tishomingo State Park, named after a Chickasaw chief. The park is home to some of Mississippi’s most rugged and picturesque topography, from massive boulders to shady crevices embellished with an embarrassment of ferns. Situated in the foothills of the Appalachians, the park contains the only Devonian and Mississippian epoch formations found in the state of Mississippi. The park’s 1,530 acres also contain trails and other features built by the Civilian Conservation Corps in the 1930s. Onward and upward from the park, the scenery remains top-notch, from wooded ridges to deep, steep hollows carved by brooks cascading over rocky streambeds. The traffic should be light, and you’ll find plenty of opportunities to stop and hike a nature trail or cool off in a clear creek.

Dishing up a brace of stunning waterfalls, a trio of outstanding overlooks, and mile after mile of deciduous forest, the northernmost section of the Trace is as hilly as it is gorgeous. Past the grave of Meriwether Lewis, who died of gunshot wounds in October 1809 in the nearby Grinder House Inn, we’ll enjoy a fun descent before confronting a challenging grade that gains 300 feet in a mile. The payoff: the splendid Swan Valley Overlook, followed by a screaming downhill to the northeastern terminus of the Trace. Afterward, we’ll celebrate with a meal of traditional Southern cuisine at the famous Loveless Café. We’ll then shuttle a few miles back into Nashville and bid farewell to one another, no doubt with an evident “trace” of sadness in our eyes.