Cycling the Natchez Trace: A Portal into a Rich Past

If there’s one thing that hits you as you’re cycling along Mississippi’s Natchez Trace, it’s the profound and deeply felt history that meets you around every bend. Even the bike route upon which your tires are humming—the scenic Natchez Trace Parkway—was literally built upon the past, thanks to local efforts to restore the well-traveled trail once followed by Native Americans, trappers, and colonial traders.

This picturesque parkway—designated a National Scenic Byway—is a 444-mile slice of cycling heaven stretching from Nashville to Natchez. It’s free of stop signs, stop lights, and cross-traffic—and off limits to commercial vehicles. The portion that VBT rides during our Mississippi: The Natchez Trace Bicycling Vacation winds past fragrant forests, fertile farms, and sweeping overlooks across the Mississippi River and Valley. This is the American South at its most authentic: a rich patchwork of glorious beauty, renowned historic sites, and some unexpected surprises.

 

An Ode to Southern Gothic: Ghostly Towns and Mansions

Abandoned in the 1930s, the eerie town of Rocky Springs provides a fascinating glimpse of life in 19th-century Mississippi. The settlement—maintained by the National Park Service—was founded in the late 1700s for the natural springs that parched the thirst of passers-through, hence its name. Yellow fever and boll weevils led to the town’s decline. Today, it is a whispering echo of its former self; among its fascinating remains, only the Methodist church is still intact.

Rocky Springs is just one ghostly relic of a rich past. As you arrive at the remains of the Windsor Plantation, you would be forgiven if you thought you were cycling into ancient Greece. It once stood proudly as a Greek Revival mansion on a sprawling 2,600 acres. During the Civil War, Confederates stationed themselves on its rooftop to look out for approaching Union soldiers. The beautiful manse survived the war, only to be burned to the ground by the embers of a reckless smoker. Elsewhere, the octagon-shaped Longwood mansion is not so much abandoned as it is unfinished. Of its intended 32 rooms, only nine on the basement level were completed, its construction interrupted by the war.

 

Two Steps Back in History: Vicksburg & the Emerald Mound

Perhaps the most significant Civil War sites in Mississippi are in Vicksburg. The city’s surrender to Ulysses S. Grant marked a turning point in the conflict. One of those sites, the Vicksburg National Military Park, offers rolling green hills for some challenging riding and historic battlefields for fascinating exploration. Both Confederate and Union soldiers are buried here, all honored by some 1,300 monuments and memorials. Onsite, the USS Cairo Museum is the final resting place of the namesake ironclad Union warship that was sunk by a mine in 1862.

Pedal further back in time at the Emerald Mound, one of the largest Native American ceremonial mounds in North America. The manmade mound was constructed from a natural hill by the Plaquemine people, ancestors of the Natchez, between the 13th and 17th centuries as pedestal-like perches for the homes of chiefs and other leaders. Excavations have uncovered skeletons, pottery, animal remains, and more relics that have given a glimpse of ancient inhabitants.

 

A Pair of Historic Institutions: Mount Locust Inn & Elizabeth Female Academy

The Natchez Trace that we travel by bicycle was once heavily traveled by horseback and by foot. Like you, those journeymen and women needed a place to eat and rest. The Mount Locust Inn & Plantation was built for that purpose. It’s been hosting travelers since 1780, though today it’s a fascinating museum that tells stories of those who came before you. One of the oldest structures in Mississippi, it’s the only surviving inn out of more than 50 that dotted the Trace in the 19th century.

Perhaps some who stayed at the Mount Locust Inn were heading to the Elizabeth Female Academy, the first educational institution for women in the state of Mississippi. Opened in 1818, it was operated by Methodists and welcomed John James Audubon as a drawing teacher in 1822. The school lasted a mere 27 years, forced to close as demographics shifted and yellow fever took hold. It was engulfed by flames in the late 1870s; today, a brick wall marks the spot of the historic site.

 

Roll into Natchez, Home to the Largest Number of Antebellum Estates in the U.S.

Natchez, perched on high ground above the Mississippi River, was spared destruction during the Civil War. As a result, history has left an impressive array of mansions built in the antebellum era, or before the Civil War. The homes are distinguished by their huge pillars and covered porches at their entrances, large windows that allowed for ventilation on hot summer days, and grand entry halls. The district that plays host to them makes for pleasant small-city cycling at the leisurely pace beloved by the South.

Stanton Hall, a Classical Revival house, is one of the most opulent not only in Natchez, but the entire Southeastern United States. This museum and National Historic Landmark was built in the 1850s by Frederick Stanton, who emigrated from Ireland and styled it after his ancestral home there. A two-story Greek temple portico, Corinthian columns, Italian marble, and glass chandeliers are just a few of its extravagant touches. Rosalie, also a National Historic Landmark, overlooks the Mississippi from a bluff. Built 30 years before Stanton, it was the inspiration for the other Greek Revival houses of Natchez. In 1863, General Grant seized it as the Union Army headquarters and had his troops pitch countless tents on the grounds.

 

Delve into the historic treasures along the Natchez Trace with us!