End of the Road

In the 1800s, travelers along the perilous forest trail known as the Natchez Trace called it the "Devil's Backbone." Today, the storied route marks the milestones—and tombstones—of sourthern history

  • By David Devoss
  • Smithsonian magazine, May 2008, Subscribe
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cypress swamps
Cypress swamps along Natchez Trace (Courtesy of the National Park Service)

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Natchez Trace trail

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The Natchez Trace: A Pictorial History

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Midnight on the Mississippi. In the antebellum city of Natchez, high on a bluff overlooking the river, lights are winking off in the Victorian mansions and plantation homes emblematic of the Old South. But down here on the riverbank, inside the Under-the-Hill Saloon, André Farish (the proprietor here until his son, André Jr., recently took over) has all night to recount some of the legends surrounding the history of Natchez. "U.S. Grant may have slept up at Rosalie Plantation, but he spent his evenings down here," Farish says, as more customers fresh off the paddle-wheeler Delta Queen push through the door. "He had one of the biggest [benders] of the war here trying to figure what to do about Vicksburg. Nobody much cared Grant was a Yankee. Natchez thought the war was bad for business."

Two centuries ago, the Mississippi city became a destination for keelboats and barges carrying commodities and manufactured goods down the river. After delivering their products and selling the barges for lumber, the boatmen, known as Kaintucks, needed a place to unwind before starting the long walk home to their Kentucky and Tennessee river valleys. They then headed north on a new route conceived and ordered built by President Thomas Jefferson, the Natchez Trace. (A trace was a forest path.) On it, Kaintucks could walk the 450 miles from Natchez to Nashville in three to four weeks. Post riders could carry mail between the two cities in about two weeks.

Today it is possible to cover the same distance in ten hours or less on the Natchez Trace Parkway, a scenic two-lane highway that parallels the Old Trace. Maintained by the National Park Service (NPS), the 444-mile road angles diagonally across Mississippi and cuts through northwestern Alabama before cresting the Tennessee Valley Divide and dropping into Nashville's Cumberland Valley. The parkway is at its most beautiful in spring and fall, when cyclists pedal beneath massive oak canopies dripping with Spanish moss and hikers follow nearby trails bordered by clover, black-eyed Susan and purple chicory. But it's beyond the parkway that the region's history truly comes alive.

With more than 600 antebellum structures, narrow streets originally designed for carriages and several districts listed on the National Register of Historic Places, Natchez, at the southern end of the parkway, boasts dozens of mansions—Magnolia Hall and Rosalie, Longwood and Auburn. They are massive showplaces, built in the early 1800s as grandiose displays of wealth by new millionaires enriched by the invention of the cotton gin.

Natchez just might be the last city in America where it's possible to purchase a piece of 19th-century America at a reasonable price. Several old houses are always up for sale, thanks in part to the Historic Natchez Foundation, a non- profit organization that buys and renovates distressed properties for eventual resale. "We're the humane society for old buildings," says Ronald Miller, an architectural historian who is the foundation's executive director.

In 1800, Natchez—founded by the French in 1716 and later populated largely by Tory refugees fleeing the Revolutionary War—stood at the edge of America's vast frontier. After the Louisiana Purchase of 1803, Jefferson envisioned further westward expansion. He decided, therefore, to bind Mississippi (and the region that would become Alabama) to the rest of the country by broadening the 450-mile forest track called the Natchez Trace.

Even on the newly widened trail, however, the journey was daunting. The route zigzagged through canebrakes, skirted cypress-filled swamps and crossed several large rivers and dozens of smaller creeks before rising 1,000 feet along ridgelines into the Eastern hardwood forest, an expanse of virgin timber so dense that according to local lore, a squirrel could travel from Maine to Texas without touching the ground. Some called the new road the "Devil's Backbone" because of recurring banditry, but the trail's rigors were the greater worry. "I have this day swam my horse five times, bridged one creek, forded several others beside the swamp we had to wade through," the Rev. John Johnson noted in 1812. "At night we had a shower of rain. Took up my usual lodging on the ground in company with several Indians."

By 1810, more than 10,000 Kaintucks rode or hiked northward each year up the Trace. At night they slept in one of perhaps 20 way stations, or rude inns, at stopping points with names like Buzzard Roost and Sheboss Place that advertised "wilderness entertainment" with "great provender and provisions." During the first three decades of the 19th century, the Natchez Trace functioned as the southwest United States' most-traveled road, although it was seldom more than 12 feet wide.


Midnight on the Mississippi. In the antebellum city of Natchez, high on a bluff overlooking the river, lights are winking off in the Victorian mansions and plantation homes emblematic of the Old South. But down here on the riverbank, inside the Under-the-Hill Saloon, André Farish (the proprietor here until his son, André Jr., recently took over) has all night to recount some of the legends surrounding the history of Natchez. "U.S. Grant may have slept up at Rosalie Plantation, but he spent his evenings down here," Farish says, as more customers fresh off the paddle-wheeler Delta Queen push through the door. "He had one of the biggest [benders] of the war here trying to figure what to do about Vicksburg. Nobody much cared Grant was a Yankee. Natchez thought the war was bad for business."

Two centuries ago, the Mississippi city became a destination for keelboats and barges carrying commodities and manufactured goods down the river. After delivering their products and selling the barges for lumber, the boatmen, known as Kaintucks, needed a place to unwind before starting the long walk home to their Kentucky and Tennessee river valleys. They then headed north on a new route conceived and ordered built by President Thomas Jefferson, the Natchez Trace. (A trace was a forest path.) On it, Kaintucks could walk the 450 miles from Natchez to Nashville in three to four weeks. Post riders could carry mail between the two cities in about two weeks.

Today it is possible to cover the same distance in ten hours or less on the Natchez Trace Parkway, a scenic two-lane highway that parallels the Old Trace. Maintained by the National Park Service (NPS), the 444-mile road angles diagonally across Mississippi and cuts through northwestern Alabama before cresting the Tennessee Valley Divide and dropping into Nashville's Cumberland Valley. The parkway is at its most beautiful in spring and fall, when cyclists pedal beneath massive oak canopies dripping with Spanish moss and hikers follow nearby trails bordered by clover, black-eyed Susan and purple chicory. But it's beyond the parkway that the region's history truly comes alive.

With more than 600 antebellum structures, narrow streets originally designed for carriages and several districts listed on the National Register of Historic Places, Natchez, at the southern end of the parkway, boasts dozens of mansions—Magnolia Hall and Rosalie, Longwood and Auburn. They are massive showplaces, built in the early 1800s as grandiose displays of wealth by new millionaires enriched by the invention of the cotton gin.

Natchez just might be the last city in America where it's possible to purchase a piece of 19th-century America at a reasonable price. Several old houses are always up for sale, thanks in part to the Historic Natchez Foundation, a non- profit organization that buys and renovates distressed properties for eventual resale. "We're the humane society for old buildings," says Ronald Miller, an architectural historian who is the foundation's executive director.

In 1800, Natchez—founded by the French in 1716 and later populated largely by Tory refugees fleeing the Revolutionary War—stood at the edge of America's vast frontier. After the Louisiana Purchase of 1803, Jefferson envisioned further westward expansion. He decided, therefore, to bind Mississippi (and the region that would become Alabama) to the rest of the country by broadening the 450-mile forest track called the Natchez Trace.

Even on the newly widened trail, however, the journey was daunting. The route zigzagged through canebrakes, skirted cypress-filled swamps and crossed several large rivers and dozens of smaller creeks before rising 1,000 feet along ridgelines into the Eastern hardwood forest, an expanse of virgin timber so dense that according to local lore, a squirrel could travel from Maine to Texas without touching the ground. Some called the new road the "Devil's Backbone" because of recurring banditry, but the trail's rigors were the greater worry. "I have this day swam my horse five times, bridged one creek, forded several others beside the swamp we had to wade through," the Rev. John Johnson noted in 1812. "At night we had a shower of rain. Took up my usual lodging on the ground in company with several Indians."

By 1810, more than 10,000 Kaintucks rode or hiked northward each year up the Trace. At night they slept in one of perhaps 20 way stations, or rude inns, at stopping points with names like Buzzard Roost and Sheboss Place that advertised "wilderness entertainment" with "great provender and provisions." During the first three decades of the 19th century, the Natchez Trace functioned as the southwest United States' most-traveled road, although it was seldom more than 12 feet wide.

Today, at Milepost 385.9, a broken stone shaft marks the grave of Meriwether Lewis. As a reward for his services, after the epic 8,000-mile exploration of the newly purchased Louisiana Territory with William Clark, Jefferson named Lewis, his former private secretary, governor of the Upper Louisiana Territory, a largely administrative job for which he was ill-suited. His discontent was compounded by his inability to find a wife and finish his written account of the journey. When the War Department demanded additional documentation for some of the expedition's expenses, Lewis decided to go to Washington.

In the late afternoon of October 10, 1809, according to various accounts later offered, Lewis pulled into Grinder's Stand on the Natchez Trace, accompanied by two servants, two heavily loaded packhorses and $100 in cash. "He seemed distraught all evening, pacing back and forth and talking like a lawyer," the innkeeper's wife later recounted. "Sometime after midnight I heard a shot and then Gov. Lewis screamed, ‘Oh Lord.' Then there was another shot."

When Mrs. Grinder entered the room she found Lewis shot in the head. A second bullet had entered his chest and lodged against his backbone. According to her version, Lewis lived through the night and "was busily engaged in cutting himself head to foot" with a razor when she entered his room the following morning. Lewis' death a few hours later initially was declared a suicide, but suspicions arose when the formerly impoverished Grinders later moved to western Tennessee with enough money to buy land and slaves.

The circumstances of Lewis' death continue to inspire debate among scholars. "He could have been murdered," says John Guice, professor emeritus of history at the University of Southern Mississippi. "Lewis carried a .69-caliber pistol. How can you shoot yourself in the head with that kind of weapon and live to get off a second shot?" In 1996, Guice, testifying at a coroner's inquest, recommended that the National Park Service disinter and autopsy Lewis. (The NPS declined to do so.)

Natchez Trace traffic began to decline in 1817, after construction began on a larger, more direct highway linking Nashville to New Orleans. But it was the steamboat that really did the Trace in. By 1820, a paddle-wheeler could make it upriver from New Orleans to Louisville in 15 days.

In 1863, after Gen. Ulysses S. Grant failed to subdue the Mississippi River stronghold of Vicksburg, he steamed south, past Jefferson Davis' plantation, and landed troops downriver. Marching up the Trace, Grant headed toward the town of Jackson. Along the way, his troops defeated a Confederate force at Raymond. Grant then torched Jackson. With his rear flank secure, Grant crossed the Trace and continued 30 miles west to Vicksburg, which he captured following a 47-day siege, on July 4, 1863 (the day after Robert E. Lee suffered a massive defeat at Gettysburg). Not until 1945, eighty-two years later, would Vicksburg's citizens celebrate American Independence Day.

In Vicksburg, where a federal military park commemorates the Union victory, it's impossible to escape memories of the siege. "People who think America has never lost a war don't realize that many of us have suffered defeat on our own soil," says Tom Pharr, a 44-year-old interior designer who owns Anchuca, an 1830 Greek Revival mansion where Jefferson Davis' brother Joseph and his family lived after Union forces looted Joseph's nearby plantation, Hurricane. (Jefferson Davis called on his brother there a couple of times in the winter of 1868-69.)

Just off the Trace in Kosciusko, a town of 7,335 (named for Tadeusz Kosciuszko, the Polish aristocrat who served under George Washington in the Revolutionary War), many residents believe that the town represents Mississippi's future. Kosciusko boasts excellent public schools, free after-school tutoring and a foundation that provides college-tuition assistance for its high-school graduates. "When people think about Mississippi, images of hooded men on horses and burning churches come to mind, but we have none of those things here," says civic leader Preston Hughes, a West Point graduate who retired from the Army as a colonel.

Credit for the community's cohesion, many agree, goes in large part to The Club, an organization that Hughes and a retired high-school principal, William White, founded in 1995. "We wanted some type of way to get together," White says. "The bank president. The janitor over at the co-op. Retirees. Young people working their first jobs. Rich. Poor. No dues. No officers. Meet once a month. Have a speaker. Ask questions. Get answers."

Kosciusko's favorite daughter is Oprah Winfrey, who was born here in 1954, but the Trace's biggest celebrity attraction is 106 miles to the north in Tupelo. There, the Elvis Presley Center includes a museum, gift shop and memorial chapel featuring continuous recordings of Elvis' gospel songs. The even bigger draw, however, is Elvis' birthplace, a tiny shotgun house built in 1934 by Presley's father, Vernon, for $180. Here, on the cramped porch, it may well be possible to come closer to the authentic Elvis—the skinny kid who loved gospel songs and often went to church—than anywhere else imaginable.

Writer David Devoss lives in Sherman Oaks, California.


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Comments (9)

The Natchez Trace, originally termed the Chickasaw Trace, was a North-South trail first formed by migratory animals and early native peoples. Native Americans such as the Chickasaw used the footpath as well as French trappers and early white settlers. The mounds along the trail range from pre-Columbian sacred places to burial mounds, proof enough that people traveled this pathway long before anyone heard of Thomas Jefferson.

Posted by Andrea Mosier on August 8,2011 | 09:28 PM

Less not forget the fact that folks used the trace to migrate when they couldn't afford other forms of transportaion. Despite what we today consider, the trace's "beauty," which is artificially maintained by the government, it was a 400-mile walk for some pioneers who endured any number of deprivations -- including lack of food, etc. A trip which took not hours, as in today, but weeks or months depending on the hardships one endured along the way. When was the last time you walked 400 miles anywhere and lived to tell about it? I salute those brave souls for their courage and perseverence.

Posted by Alex Colvin on January 20,2010 | 01:18 PM

I enjoyed this article very much, especially the posted comment about Grant staying at the Waverly mansion, owned by John B. Peyton, a distant cousin of mine. Jim Peyton

Posted by Jim Peyton on March 30,2009 | 06:54 PM

Interesting article. On his way to Jackson at the Battle of Raymond, Grant and his troops encamped at Waverly, a large plantation home built by John B. Peyton, my third great grandfather. It is said that Aunt Anne Peyton entered the room where Grant and his officers were quartered and she demanded that the general return their cows and oxen and not take any more food from the children. Grant, evidently taken aback, wrote an order to his troops to not take anything from the Peytons and he and his troops shortly left their home.

Posted by Sandy McDonough on May 14,2008 | 08:00 AM

I agree with Iris... the Choctaw, Chickasaw & other Southeastern Tribes were traveling the trail long before the Kaintucks showed up...

Posted by Glenda Raymond on May 8,2008 | 12:36 AM

The Natchez Trace (once known as the chickasaw trail) was not the "end of the road" it was actually the start of the trace which ended in Nashville. Travelers would come down river to Natchez then journey back on the Trace. Not the other way around. Also, I think there are around 400 antebellum structures in Natchez not over 600.

Posted by Harry Boschieri on May 6,2008 | 11:42 AM

Lovely story about the Natchez Trace, but no mention of the original owners--the Choctaw Indians. How sad.

Posted by iris ellison on May 1,2008 | 04:33 PM

as a student of southern history, i have many times been on the trace from Natchez to Nashville. i have wanted to start a photo essay about this beautiful park and the landscape. look for some of my pictures (hopefully) about the trace. Billy M. Hines

Posted by billy hines on May 1,2008 | 04:11 PM

END OF THE ROAD: The informative, creative writing of David Devoss has captured my own imagination: As a published writer myself, the content, its passion and spell binding history has inspired some literary thoughts about the 'South' In fact, will begin writing tomorrow! Thank you for the stimulating, authenic look at one of the curios of our first States. I.Jean Pastula PhD

Posted by I. Jean Pastula PhD on May 1,2008 | 02:45 PM




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