Old Southwest Highway
- Date Wed 4th March 2026 - Sun 8th March 2026
- Time 2:00PM CST
- Location Tupelo, Mississippi
- Price $2,027.96 - $2,339.96
- Races 2 races
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Event summary
Get ready for an exhilarating cycling adventure at the Old Southwest Highway event, taking place from March 4th to March 8th, 2026, in the vibrant city of Tupelo, Lee County. This unique spring training retreat invites cycling enthusiasts to explore scenic routes and enjoy the warm southern hospitality that the region is known for. Riders will experience a range of distances, with daily rides including 40 miles on the Old Gulf & Ship Island railbed, an impressive 85-mile journey into Alabama, and a final 65-mile ride culminating at the iconic 440-mile marker.
Participants will benefit from four nights of comfortable accommodations, savor delicious classic southern meals, and enjoy top-notch support with roving sag ride leaders and well-stocked aid stations. The event kicks off with transport from Nashville to New Albany, setting the stage for an unforgettable cycling experience. Whether you’re a seasoned rider or just looking to enjoy the beautiful landscapes, the Old Southwest Highway promises an uplifting, memorable journey through the heart of the South. Don't miss this chance to ride where the King of Rock and Roll hails from! Full details are available at FASTENDURANCE.com/natchez.
Participants will benefit from four nights of comfortable accommodations, savor delicious classic southern meals, and enjoy top-notch support with roving sag ride leaders and well-stocked aid stations. The event kicks off with transport from Nashville to New Albany, setting the stage for an unforgettable cycling experience. Whether you’re a seasoned rider or just looking to enjoy the beautiful landscapes, the Old Southwest Highway promises an uplifting, memorable journey through the heart of the South. Don't miss this chance to ride where the King of Rock and Roll hails from! Full details are available at FASTENDURANCE.com/natchez.
Organiser's Description
Straight out of the home of the King of Rick and Roll comes this hidden gem. With an Olympic Size pool, quiet roads, flowing trails, and great weather this is a spring training paradise.
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
