Adventure Cycling Association

We’ll initiate our 460-mile journey by meeting in Nashville, Tennessee, the capital of country music. Arrive early to take in the Ryman Auditorium, Johnny Cash Museum, and even a replica of the Parthenon. Then, meet up with your fellow adventurers to go over maps, make last-minute adjustments to your bikes, enjoy your first meal together, and rest for the long drive to the beginning of your ride tomorrow.

Every journey begins with the first step, and this one starts with a drive through bucolic Southern countryside as we make our way towards the historic town of Natchez, Mississippi. The town was established by French colonists in 1716 and was capital of the Mississippi Territory until 1822. it was also 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, many would walk home to the Ohio River Valley by way of the Natchez Trace rather than fight the river’s currents. After a shakedown, self-guided tour around Natchez, we will gather 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. Our first day on the Trace will be an easy one, providing additional time to visit the sites of Natchez and the 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 used it for ceremonial purposes. Later in the day, we’ll make a short 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, 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. We’ll also take time to explore the Clinton Visitor Center, which was built with period materials and architectural details to give 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’ll end the day at a Ridgeland hotel just north of the capital.

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, especially in and around the hills near our campground. Opportunities to rest 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 French Camp, the Trace rolls through the Red Clay Hills before settling into bottomlands near the headwaters of the Big Black River. Another pivotal battle was contested near this waterway when Union forces under Grant defeated Confederate troops led by General John C. Pemberton. The miles will seem to zip along, with only a handful of minor hills and few changes in the nearly 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 route today.

Early in the day, we’ll skirt Tupelo, the birthplace of Elvis Presley. 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 to the Old Town Overlook and Chickasaw Village Site. The rest of the day is 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 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. You’ll also find the only Devonian and Mississippian epoch formations found in the state of Mississippi as well as 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 have plenty of opportunity to stop for a hike 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’s Stand, 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 and a screaming downhill to the northeastern terminus of the Trace. Afterward, we’ll celebrate with a traditional Southern meal at the famous Loveless Café. Then, we’ll shuttle a few miles back into Nashville and bid farewell to one another, no doubt with a “trace” of sadness in our eyes.