Old Southwest

Highway

     March 5-8, 2026     

All Inclusive Price - $1,949

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A winding road through a forested area under a clear blue sky.

“No stop signs, no turns, no nee for brakes and no worries. Just clip in and roll.”
~ Rob

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Itinerary*

Two cyclists, one older man and one younger woman, standing on a grassy field with trees in the background, holding their bikes above their heads in celebration.
Group of cyclists wearing matching black and red cycling jerseys, helmets, and sunglasses, standing with their bikes outside a building during daytime.

The adventure begins March 4 with a transfer from either Memphis International or Trace Bike Shop in Nashville to the starting accommodations in New Albany, MS.

March 5 - Start the tour heading south on the old Gulf and Ship Island paved railroad bed. Once operated by 36-inch steam driven wheels, they 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 cyclist’s dream rolling through farmland of the deep south.

A group of cyclists riding on a rural road through a forested area.
A white Orbea road bicycle parked against a metal railing on a bridge next to a large body of water and distant green shoreline under a partly cloudy sky.

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.

A person riding a bicycle on a winding road through a wooded area in autumn or winter.
A group of cyclists riding on a road through a wooded area during sunset.

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. 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.

Group of cyclists riding on a paved road through a green rural area with trees and grass, during daytime.
A cyclist riding a road bike along a winding mountain road next to a rocky cliff with lush green vegetation.

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.

*-Itinerary may be improved tailored to closures, participants ability levels, and projected weather.

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Map showing a route from Birmingham, Alabama to Nashville, Tennessee marked with numbered red circles connected by a red line.

    • 4 Nights hotel

    • 4 Breakfasts, 3 Lunches, & 3 Dinners

    • Transfer from Nashville or Memphis to New Albany

    • Gear Transport

    • Stocked & Staffed Aid Stations

    • On Call Sag Support

    • Airport or Nashville → New Albany Transfer

    • Wake up to a relaxing breakfast at or near the hotel.

    • During breakfast our staff will ensure that your device has the days course uploaded.

    • After breakfast repack your luggage and pack a day bag. Our staff will load your luggage in a van bound for the next hotel. Day bags will be loaded in a van bound for aid station #2.

    • Each morning ride will roll out in 1 single group or in waves based on terrain, ability level, and group size.

    • The 1st aid stop will be our coffee stop.  This will be between 1/3 & 1/2 way and will have coffee, sports drink, water, bananas, bars, and gels.

    • The 2nd aid stop will be our lunch stop. This will be between 2/3 & 3/4 of the way. This stop will have sandwiches and finger foods (chips/pretzels), sports drink, water, gels, bars, and your day bag.

    • Upon arrival to the hotel riders will be met with our staff who will hand out room keys and share dinner plans.

    • Dinner will be at a local restaurant or catered to hotel.

  • Day 1 - 85 (60, 45) miles, Flat
    Day 2 - 85 (50, 30) miles, Flat
    Day 3 - 60 (45, 20) miles, Rolling
    Day 4 - 65 (45, 25) miles, Rolling
    Trip Total - 300 miles & 15k’ elevation

  • The ride will begin & end @ Trace Bikes in Nashville.

    Meet ~7pm on Wednesday Evening
    Return ~noon on Sunday

  • Average high 60
    Average low 45

    March tends to be breezy and dry.

  • 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.

  • 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

Register Here!

Register Here!