Stretching from Natchez, Mississippi to Nashville, Tennessee, the Natchez Trace Parkway is one of North America’s hidden gems for cyclists. Riding here feels like pedaling along a 440-mile bike path with no stoplights, no commercial traffic, and few interruptions. Just smooth pavement, beautiful scenery, and mile after mile of relaxed, uninterrupted riding.

With its vast stretches of twisty roads and little vehicle traffic, its tremendous scenery over ridges and through isolated hollows, its undulating terrain with no huge climbs, and its myriad of small friendly towns steeped in history, it’s no wonder that the Natchez Trace (also known simply as “The Trace”) is a destination for many cyclists looking to reconnect with nature while pursuing their love of cycling.

Also known as the “Old Natchez Trace”, the historical footpath that extends roughly 440-miles from Natchez, Mississippi, to Nashville, Tennessee. The Trace was first created by migrating animals and then used for centuries by Native Americans. After the Americas were founded, The Trace was later used by early European and American explorers, traders, and emigrants in the late 18th and early 19th centuries. Today, the trail is commemorated by the 440-mile Natchez Trace Parkway which follows the approximate path of the old Trace.

Unlike many other outfits offering week-long cycling tours along the Natchez Trace Parkway, we did our research and discovered that a South to North tour is just a better experience. Here are a few reasons why:

Why Ride the Natchez Trace from South to North?

• Mile Markers – Mile Marker 0 starts in Natchez, MS & Mile Marker 444 ends in Nashville, TN. It’s more fun to add up miles rather than count down!
• Sun – Lights your way, rather than blinds you
• Tailwind – The prevailing winds in this region come from the South to Southwest
• History – Of  the 1800’s boatsmen who repeatedly traveled down the Mississippi River and back up the Trace
• Seasonal Cycle– Riding from South to North along the Natchez Trace in early autumn is a metaphorical transition from a summer into autumn season
• Fitness – Progress naturally with easier ‘training’ early on
• Easier Logistics 

• Duration: 7-days

• Ride Type: Road

• Difficulty: Intermediate / Intermediate+

• Average Daily Mileage: 43 -63

• 440 miles of riding with no cars
• Charming towns
• Sunken Trace
• Elvis Presley Birthplace
• The Belmont Hotel
• Meriweather Lewis National Monument

Day 0 is the day before the tour begins. Final logistics will be provided in your confirmation documents.

Guests typically fly into Jackson–Evers International Airport (JAN) and travel to Natchez, MS, where the tour begins. A pre-arranged shuttle from Jackson to Natchez is available with advance reservation and includes transport for you, your gear, and your bicycle.

We recommend arriving earlier in the day to allow for potential flight delays. Guests are responsible for reserving their own accommodations in Natchez on the evening before the tour begins.

47 miles | up to 1,940 feet of climbing

Day one begins with a brief welcome, bike fitting, and overview of the week ahead. After loading gear into the support vehicle, we ride to the southern terminus of the Natchez Trace Parkway and begin our journey north.

Today’s shorter ride allows everyone to settle in while enjoying highlights along the route, including a short detour to Emerald Mound, an ancient ceremonial site built by the ancestral Natchez between 1200 and 1730 A.D., and a stop at Mount Locust, the last remaining historic stand along the Trace.

After a relaxed lunch stop, we continue riding past the beautiful town of Port Gibson before finishing the day at Sunken Trace, a preserved section of the original Natchez Trace pathway. From there, we shuttle a short distance to Vicksburg, where we check in and enjoy the evening.

64 miles | up to 2,140 ft of climbing

After breakfast, we shuttle back to the Natchez Trace Parkway and begin riding from Sunken Trace. The morning includes a stop at Rocky Springs, the site of a historic ghost town.

The route winds through hardwood forests and open countryside with lunch at Dean Stand and a short stop at the Clinton Visitor Center. From there, we ride the final miles along the Chisha Foka Trail before finishing the day in Ridgeland, Mississippi.

83 miles | up to 1,485 ft of climbing

Today’s ride covers one of the flatter sections of the Natchez Trace, allowing the miles to pass quickly. We begin along the Chisha Foka Trail before joining the Parkway and riding beside Barnett Reservoir, where wildlife sightings are common.

Stops include Cypress Swamp, with its boardwalk through tupelo and bald cypress trees, and lunch in Kosciusko. The day ends at the French Camp Historic District, a reconstructed log-cabin village in one of Mississippi’s most remote areas.

88 miles | up to 2,350 ft of climbing

Today is the longest ride of the tour, beginning with an early start along the quiet Natchez Trace through the scenic Red Clay Hills. Along the way we pass the Bynum Mounds, ancient burial mounds dating from 100 B.C. to 100 A.D.

The ride finishes at the Natchez Trace Parkway Visitor Center before continuing to Tupelo, Mississippi, birthplace of Elvis Presley, where we spend the evening.

55 miles | up to 2,500 ft of climbing

The day begins in Tupelo with a visit to the Elvis Presley Birthplace before shuttling back to the Natchez Trace to continue riding north. Along the route we stop at the Pharr Mounds, an ancient Native American burial complex dating from 100–200 A.D.

After crossing the Tennessee–Tombigbee Waterway and entering Alabama, the ride ends near Cherokee. From there we shuttle to Florence, with a highlight stop for a guided tour of the legendary Muscle Shoals Sound Studio before settling in for the evening.

68 miles | up to 2,375 ft of climbing

After shuttling from Florence, we return to the Natchez Trace and ride through wooded ridges and scenic stream valleys, reaching the highest point on the Trace at 1,100 feet.

A short detour brings us to the Wichahpi Commemorative Stone Wall, built by Tom Hendrix to honor his great-great-grandmother’s journey during the Trail of Tears. The ride ends at the Meriwether Lewis National Monument, followed by a shuttle to our accommodations in Linden, Tennessee.

57 miles | up to 3,775 ft of climbing

The final day begins with a shuttle from Linden back to the Meriwether Lewis National Monument before starting the last ride along the Natchez Trace.

This scenic final section features rolling hills, sweeping curves, and the iconic Double Arch Bridge. The ride ends at the Northern Terminus of the Natchez Trace, followed by a shuttle to Nashville, where the tour concludes.