Old Southwest
Highway
March 5-8, 2026
Price - $1,999
“Lock in and roll. No brakes and no worries.”
~ Rob
Itinerary
March 4 accommodations included in New Albany, MS.
March 5 - Starting the tour heading south on the old Gulf and Ship Island paved railroad bed. Once operated by 36 inch steam driven wheels, are now exchanged for 29” man powered wheels. At the end of the trail riders will roll into a decadent brunch. After fully refueling on southern hospitality. Riders will roll onto the Natchez Trace following the trade routes of the Natchez, Chickasaw, and Choctaw nations. In the 1800’s this route became known as the Old Southwest. Today it is a motorway that has no stop lights, stop signs, nor turns. Simply a cyclists dreams rolling through farmland of the deep south.
March 6 - The day starts with a visit to Elvis Presley’s birthplace and museum. See where the king started off before transforming rock and roll. Then riders will trade in their imaginative guitar strings for wheels as they rejoin the Natchez Trace. Rolling past multiple mound sites signifying native villages dating back to the BC era. Before long riders will leave Mississippi behind and welcome in Alabama sunshine. The day wraps up crossing the Tennessee River and rolling along the Tennessee River delta.
March 7 - The day rolls out heading out of the Tennessee river valley and back onto the Natchez Trace. Within a few miles riders will cross into Tennessee and will quickly notice a change in terrain as the terrain. The flatter farmland gives way to wooded lined roads with ever growing rollers. The final miles of the day pass through Laurel Hill Wildlife Management Area before kicking back fireside for a fireside meal.
March 8 - The final day starts out with a fireside breakfast and an easy spin to Merriweather Lewis’ tomb. Then it is all eyes on mile marker 440, the end of the trace. The ride rolls on in more ways than one. The hills will grow into small climbs as the riders near Nashville crossing over the Tennessee Valley Divide. Then the final miles are spent descending down toward Nashville where the ride concludes just past the Trace terminus. Here riders can catch a shower and get cleaned up before heading to the airport or home in their vehicles.
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4 Nights hotel
4 Breakfasts, 3 Lunches, & 3 Dinners
Gear Transport
Stocked & Staffed Aid Stations
On Call Sag Support
Airport or Nashville → New Albany Transfer
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By Car -
Depart Nashville, TN 6 pm March 4By Air
Arrive MEM March 4
Depart BNA March 9 after 2pm
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Average high 60
Average low 45March tends to be breezy and dry.
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Day 1 - 85 miles, Flat
Day 2 - 85 miles, Flat
Day 3 - 60 miles, Rolling
Day 4 - 65 miles, Rolling
Trip Total - 300 miles & 15k’ elevation -
We call it our escalator. Jump in the van and make the day achievable. We will transport you to the first aid station if you would like to start ahead. We can bring you from the 1st to 2nd aid to break up the day.
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We recommend a road bike.
E-bikes with Batteries over 700Wh are welcome. We will support you on the journey but can only provide limited sag support due to the weight of an e-bike. -
Single Occupancy
Bike Rental
Post Ride Food & Snack Service
Bike Build & Rebox
Personal Domestique