Old Southwest Highway
When is Old Southwest Highway?
Old Southwest Highway takes place on Wednesday, March 4, 2026 in Tupelo, MS.
What distances does Old Southwest Highway offer?
Old Southwest Highway offers 2 events: Single Occupancy, Double Occupancy.
| Event | Distance | Price | |
|---|---|---|---|
| Single Occupancy | — | $2199.00 | Register |
| Double Occupancy | — | $1899.00 | Register |
How much does Old Southwest Highway cost?
Registration for Old Southwest Highway starts at $1899.00. Prices vary by event distance.
Where is Old Southwest Highway held?
Old Southwest Highway is held in Tupelo, MS at 2680 Natchez Trace Parkway.
About Old Southwest Highway
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