Old Southwest Highway
- Date Wed 4th March 2026 - Sun 8th March 2026
- Time 2:00PM CST
- Location Tupelo, Mississippi
- Price $2,183.96 - $2,391.96
- Races 2 races
Event summary
Join us for the exhilarating Old Southwest Highway cycling event, taking place from March 4th to March 8th, 2026, in the beautiful Tupelo, Lee area. This unique five-day adventure invites cyclists to traverse a historic trade route once used by the Choctaw, Chickasaw, and Natchez tribes, all while enjoying the stunning spring bloom as they ride from Mississippi to Nashville.
Participants can look forward to a fully supported journey featuring a variety of race distances, including 40 miles on March 5, an impressive 85 miles on March 6, a scenic 60 miles on March 7, and a final 65-mile stretch on March 8. Along the way, riders will be treated to delightful Southern cuisine, comfortable accommodations, and the camaraderie of fellow cycling enthusiasts. With a maximum 6:1 rider-to-leader ratio, you can rest assured that expert guidance and support will be readily available. Don't miss this chance to experience the rich history and natural beauty of the region while pushing your limits on two wheels! For full details, visit FASTENDURANCE.com/natchez.
Participants can look forward to a fully supported journey featuring a variety of race distances, including 40 miles on March 5, an impressive 85 miles on March 6, a scenic 60 miles on March 7, and a final 65-mile stretch on March 8. Along the way, riders will be treated to delightful Southern cuisine, comfortable accommodations, and the camaraderie of fellow cycling enthusiasts. With a maximum 6:1 rider-to-leader ratio, you can rest assured that expert guidance and support will be readily available. Don't miss this chance to experience the rich history and natural beauty of the region while pushing your limits on two wheels! For full details, visit FASTENDURANCE.com/natchez.
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
2pm or 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.
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
2pm or 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.
Full details available at FASTENDURANCE.com/natchez
Races
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Location
2680 Natchez Trace Parkway, Tupelo, 38804, MS, United States
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Old Southwest Highway
