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Southern Natchez Trace

More than a Scenic Ride
Price :
Surface :
Duration :
8 days
Support :
Fully Supported
Difficulty :
Level 3

Come experience cycling the best of the Southeast. Travel along the scenic recreational Natchez Trace Parkway from Ridgeland to Natchez, a southern jewel of a town. We will continue our journey through verdant farmlands to Port Gibson, the town “too beautiful to burn,” visiting Windsor Ruins along our way. We’ll overnight at Grand Gulf State Park, which some refer to as the “Little Grand Canyon,” a park known as one of the natural wonders of the Ozarks.  We spin on to the historic Civil War city of Vicksburg and visit the Vicksburg National Military Park, the key to the Civil War.

Soak up the scenes of Spanish moss–draped trees, enjoy catered meals that reflect the best of this region’s culinary tradition, and learn about the past and present of this corner of the country.

e-bike friendly: Click to read our FAQ

Grab some friends and join today! Each rider in a group of 5 or more will receive a 15% discount. Learn more...

Photos by Sharon Korstick | Alan Brown | Arlen Hall
Oct 17 - Oct 24, 2021
Space still available

"The meals were fantastic and the support by the trip leaders was as good as anything I have experienced on far pricier tours."


Day 1. Ridgeland, Mississippi, 0 miles

We'll meet in Ridgeland, a scenic suburb north of Mississippi's capital city, to get acquainted with our tour leaders and one another. If you arrive early, prepare to be wowed by the cycling culture here that has fallen head over heels for two (and three!) wheels. Check out the Ridgeland Multi-Use Path and Natchez Trace Multi-Use Trail, then settle in for a map meeting and a restful night before we embark on our justly famous route in the morning.

Day 2. Ridgeland to Rocky Springs, 49 miles

After we leave our hotel in Ridgeland, set your own pace as we cycle south along the pastoral Natchez Trace Parkway. As we pass through Clinton, take a few minutes to stop by the visitor center, with a museum highlighting the history of the Trace and Clinton. As you continue south, you will see the historic location of the Battle of Raymond, where General Ulysses S. Grant's troops clashed with the Confederate brigade of General John Gregg on May 8, 1863. Pedal through history at Dean's Stand, where General Grant made his headquarters after the Battle of Raymond, and Red Bluff Stand, which previously served as the boundary between the Choctaw tribe and three different nations: France, Spain, and the U.S.

Day 3. Rocky Springs to Natchez, 61 miles

Today you will continue your bike travel along the Natchez Trace Parkway to the southernmost terminus in Natchez. Spanish moss hangs from the trees, and the scenery varies from hardwood forest to open pastures and cotton fields. Soon you'll pass the Sunken Trace, a preserved section of the original route where you can easily imagine a lone horseman appearing around the bend on his arduous wilderness journey. Your day's journey will end at our campsite along the mighty Mississippi River.

Day 4. Layover day in Natchez, 0 miles

Today you will have the opportunity to experience all that historic Natchez has to offer. First, stop at the Natchez Visitor Center to watch the engaging history of Natchez film and plan your day. Take a few moments to visit St. Mary Basilica in the heart of Natchez, the city's central landmark, known as an architectural masterpiece among the South's Catholic churches. Or relax and enjoy the hospitality at one of the downtown cafés. This day is yours to enjoy.

Day 5. Natchez to Port Gibson, 64 miles

Today we'll leave the Trace and venture off the parkway onto the backroads of Mississippi. We'll ride past Alcorn State University, founded in 1871 by the Reconstruction-era legislature. Along your route, you will visit the Windsor Ruins, built in the mid-1850s, a plantation that once sprawled over 2,600 acres and now looms like a Roman ruin thanks to the 23 still-standing columns. The day will end near Port Gibson, the city General Grant called "too beautiful to burn."

Day 6. Port Gibson to Vicksburg, 44 miles

Enjoy today's ride on a peaceful country road as we drop into the Big Black River floodplain. We'll end today's ride in the town of Vicksburg, site of a turning point in the Civil War when Union forces laid siege to the city for 47 days.

Day 7. Layover day in Vicksburg, 0 miles

There are plenty of layover day options here, including a scenic and historic bike tour of the Vicksburg National Military Park, a walking tour of the charming downtown area and surrounding historic district, or strike out on your own to see this unique Southern city.

Day 8. Vicksburg to Ridgeland, 52 miles

Your final day takes you back to Ridgeland via Old U.S. 80 along rural roads through pastures, cotton fields, and forests, passing the sometimes forgotten towns of Bolton, Edwards, and Bovina. Ride through history as Union troops marched through this area after capturing the city of Jackson. Arrive back in Ridgeland with a new appreciation for this area's complicated past and its potential future as a bicycling destination.


Additional Details
Start Location:
Ridgeland, MS
End Location:
Ridgeland, MS
Jackson Medgar Wiley Evers Intl. (JAN)
Total Days:
Riding Days:
Layover Days:
Tour Leader:
Average Daily Mileage:
Camping, Motel Options
Catered meals
Level 3

Know before you go

Information for eBike riders:
Because every rider, eBike, road condition, and elevation profile is different, it is ultimately up to the participant to judge best whether their battery will last through each tour day. We recommend using pedal assist in its lowest setting or off when not needed to maximize battery range. Bringing a second battery is also recommended. They can be carried by staff on our fully supported events, but will need to be carried by the participant on our inn-to-inn trips.