Old Southwest Highway
- Date Wed 4th March 2026 - Sun 8th March 2026
- Time 2:00PM CST
- Location Tupelo, Mississippi
- Price $2,392.90 - $2,703.96
- Races 2 races
Event summary
Join us for the exhilarating Old Southwest Highway cycling event from March 4th to March 8th, 2026, in the charming town of Tupelo, Lee County, Mississippi! This unforgettable journey takes cyclists along historic routes once traveled by the Choctaw, Chickasaw, and Natchez tribes, offering breathtaking views of ancient mounds as spring blooms beautifully across the landscape.
With a total of 440 miles of scenic rides, participants will experience a variety of challenging distances, including a 40-mile ride on the first day, followed by an incredible 85-mile trek into Alabama, and culminating with a final 65-mile ride into Tennessee. Riders will enjoy four nights of comfortable accommodations, delicious Southern meals, and the support of dedicated roving sag ride leaders, ensuring a memorable experience for all skill levels. Don't miss this opportunity to embrace the spirit of adventure and explore the rich cultural history of the region while enjoying the thrill of cycling!
With a total of 440 miles of scenic rides, participants will experience a variety of challenging distances, including a 40-mile ride on the first day, followed by an incredible 85-mile trek into Alabama, and culminating with a final 65-mile ride into Tennessee. Riders will enjoy four nights of comfortable accommodations, delicious Southern meals, and the support of dedicated roving sag ride leaders, ensuring a memorable experience for all skill levels. Don't miss this opportunity to embrace the spirit of adventure and explore the rich cultural history of the region while enjoying the thrill of cycling!
Organiser's Description
Just bring your bike and we got the rest. For a thousand years this was the trade route that joined the Choctaw, Chickasaw, and Natchez tribes. Now cyclists will get to enjoy views of ancient mounds as the spring bloom begins heading Northeast from Mississippi to Nashville.
INCLUDES
4 Nights Accomodations
4 Dinners of Classic Southern Food
3 Lunches
Transport from Nashville to Start in New Albany
Roving Sag
Ride Leaders max 6:1 ratio
Aide Stations stocked with sports drinks, Gels, Bars, Cola, & Water
ITINERARY**
March 4
7pm - Meet at Trace Bike Shop for Transport to New Albany
(4 hour Van ride with 1 bathroom stop)
March 5
Start the day riding South on the Old Gulf & Ship Island railbed. After 40 miles stop for a decadent brunch. Then remount and join the Natchez trace for a 45 mile ride to Tupelo.
(Shorter ride option will be to only ride the 2nd ride)
March 6
The day begins with a trip to Elvis Presley's birth place. Then it is on to 2 wheels Alabama bound for an 85 mile day. The day ends rollng along the Tennessee River delta.
(Shorter ride option of 50 miles)
March 7
Rolling into Tennessee the roads become tree lined and rolling. The day is 60 miles and ends with fireside cooking.
March 8
All eyes are set counting down to the 440 mile marker post which signifies the end of the day. It is a 65 mile day and most riders are done and on the road home, or headed to the airport, by 1pm.
** - Subject to be tweaked & improved to tailor the trip to those participating.
Full details available at FASTENDURANCE.com/natchez
INCLUDES
4 Nights Accomodations
4 Dinners of Classic Southern Food
3 Lunches
Transport from Nashville to Start in New Albany
Roving Sag
Ride Leaders max 6:1 ratio
Aide Stations stocked with sports drinks, Gels, Bars, Cola, & Water
ITINERARY**
March 4
7pm - Meet at Trace Bike Shop for Transport to New Albany
(4 hour Van ride with 1 bathroom stop)
March 5
Start the day riding South on the Old Gulf & Ship Island railbed. After 40 miles stop for a decadent brunch. Then remount and join the Natchez trace for a 45 mile ride to Tupelo.
(Shorter ride option will be to only ride the 2nd ride)
March 6
The day begins with a trip to Elvis Presley's birth place. Then it is on to 2 wheels Alabama bound for an 85 mile day. The day ends rollng along the Tennessee River delta.
(Shorter ride option of 50 miles)
March 7
Rolling into Tennessee the roads become tree lined and rolling. The day is 60 miles and ends with fireside cooking.
March 8
All eyes are set counting down to the 440 mile marker post which signifies the end of the day. It is a 65 mile day and most riders are done and on the road home, or headed to the airport, by 1pm.
** - Subject to be tweaked & improved to tailor the trip to those participating.
Full details available at FASTENDURANCE.com/natchez
Races
-
Single Occupancy
Incl. $104.96 Fee
Wed 4th March 2026 (2:00PM CST)
$2,703.96
CLOSED -
Double Occupancy
Incl. $93.00 Fee
Wed 4th March 2026 (2:00PM CST)
$2,392.90
CLOSED
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Location
2680 Natchez Trace Parkway, Tupelo, 38804, MS, United States
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Old Southwest Highway
