Cycle through history, nature, and Southern charm along the Natchez Trace Parkway

Spring blooms, comfortable temperatures, and gentle humidity set the stage for an unparalleled Natchez Trace cycling adventure on what many call America’s most pristine biking route. If you love cranking out miles on a stunning national parkway steeped in beauty and history, look no further. This is the ride for you!

The Natchez Trace Parkway winds through three states and more than 10,000 years of history. It follows the route of the Old Natchez Trace, a historic travel corridor once used by American Indians, early settlers, traders, and even future presidents. Linking the Cumberland, Tennessee, and Mississippi Rivers, the Parkway offers a captivating blend of natural splendor and historical depth.

Building on what we learned from our 2025 rides, the 2026 Natchez Trace Parkway bike tour features a refined itinerary that balances daily mileage and shorter shuttle transfers at the end of each riding day. You'll enjoy charming Southern communities, rich regional culture, and, as everyone knows, some serious Southern cooking, y’all!

The ride assembles in Franklin (Nashville), Tennessee on Sunday afternoon for the pre-check-in. Early Monday we shuttle to the iconic Double Arch Bridge at Birdsong Hollow, marking the start of your seven-day bike tour to Natchez, Mississippi. Once in Natchez, we'll enjoy some time exploring this delightful river town before beginning our return north, in order to make Monday's drive back to Franklin, TN, shorter and more relaxed.

Starting from mile marker 440 we’ll cycle over the Double Arch Bridge at Birdsong Hollow embarking on a scenic 62 mile journey to Jack’s Branch. After a short shuttle to Lawrenceburg, TN we’ll settle into the new Best Western Plus for the night.

From Jack’s Branch, the journey continues with a picturesque 70-mile ride into Alabama. En route you’ll cross the impressive John Coffee Memorial Bridge, the parkway’s longest, enjoy stunning views as you pedal to Cave Spring. The night will be spent at a Bed and Breakfast in Belmont, MS.  Established in 1977, the Sparks Drive Inn Restaurant is a longstanding community anchor, and the food is to die for, hence we’ll enjoy two meals there!

The longest cycling day, pedal 75 miles from Cave Spring to Witch Dance. Explore pre-Columbian history with stops at Bear Creek Mound and Pharr Mounds, featuring ancient earthworks dating 1,800 to 2,000 years. We will also SAG you at the Parkway Visitor Center where you can take in the history of the Natchez Trace. Shuttle for no more than 10 minutes into Houston, MS for the night.  We have a special treat for you on Thursday morning - the most amazing donuts we've ever tasted - to kick-start your day of riding.

Our second longest riding day spans 74 miles from Witch Dance to Kosciusko.  Your efforts will be rewarded with tasty cinnamon buns upon arrival in French Camp. After indulging, pedal directly to your hotel room in Kosciusko to relax before dinner.

On the fifth day of riding, saddle up from the hotel and embark on a pedal to the biggest city off the trail, Ridgeland\Jackson, MS.  Those on the 5 day ride will say bon-voyage at the 37th mile and here is where the Natchez option extends your ride.  We’ll ride into Ridgeland for the night. Total miles for the day will be 61.

The busy streets of Ridgeland soon fade behind you as you return to the springtime tranquility of the Natchez Trace. Today’s 63-mile ride unfolds over gently rolling hills, offering a peaceful rhythm and classic Trace scenery on your way to Port Gibson, Mississippi.

Upon arrival, we’ll settle in at the welcoming Isabella Bed & Breakfast. After checking in, we can visit the nearby Windsor Ruins, one of Mississippi’s most iconic landmarks. The haunting remains of massive columns still stand after a devastating fire in 1890. 

A perfect way to wrap up this memorable journey, with just 47 miles to the official finish in Natchez, Mississippi. Along the way, take time to visit Emerald Mound, the second-largest ceremonial mound from the Mississippian Period in the United States. Once in Natchez, enjoy some time to explore this charming river town before we begin our return shuttle north of about two hours, reducing the next day's drive back to Franklin.

After an early morning breakfast, we’ll shuttle back to the host hotel in Nashville/Franklin, TN.  The journey, with breaks, will take approximately six hours, so be sure to pre-load your podcasts and enjoy some well-earned rest along the way.