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

Early November’s cooler temperatures and the vibrant colors of autumn create the perfect setting for an unparalleled cycling adventure on what is widely hailed as America’s most pristine biking route.  If you love long rides through scenic national parkways, this is the journey you’ve been waiting for!

The Natchez Trace Parkway is a recreational and scenic route stretching across three states and 10,000 years of history. It roughly follows the “Old Natchez Trace”, a historic travel corridor used by American Indians, early settlers, and future presidents. Linking the Cumberland, Tennessee, and Mississippi Rivers, this scenic parkway offers a captivating blend of natural beauty and historical significance.

The 2025 ride offers an even more seamless experience, as the road construction on the Natchez Trace Parkway was officially completed in 2024.  We’ve fine-tuned the itinerary to strike a better balance between daily mileage and shorter shuttle distances, making each day more enjoyable. And, of course, the Southern charm of the communities we pass through, along with the local cuisine, will leave you full in more ways than one. 

The ride assembles in Columbia, Tennessee (south of Nashville) on Wednesday afternoon for the pre-check-in. Early Thursday, we shuttle to the iconic Double Arch Bridge at Birdsong Hollow, the official starting point of your seven-day cycling adventure to Natchez, Mississippi. After your final ride on the following Wednesday, we'll spend a night in French Camp before shuttling back to Columbia, TN early Saturday morning.

Starting from mile marker 440 we’ll cycle over the Double Arch Bridge at Birdsong Hollow embarking on a scenic 63 mile journey to Jack’s Branch. After a shuttle to Lawrenceburg, TN we’ll settle into their 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 76 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. We’ll ride into Ridgeland for the night. Total miles for the day will be 61.

The busy streets of Ridgeland will soon fade behind you and you’ll return to the autumn tranquility of the Natchez Trace for a day of gently rolling hills on the 63-mile spin down to Port Gibson, MS. Once in Port Gibson, we’ll settle in for a night stay at Isabella Bed & Breakfast. After checking in, we’ll make a visit to Vicksburg.

A perfect way to end this epic ride, with just 47 miles to the official finish in Natchez, MS. Along the way, make sure to stop and admire Emerald Mound, the second-largest Mississippian Period ceremonial mound in the United States. Once in Natchez, you’ll have time to explore before shuttling to French Camp for the night.

After breakfast in French Camp, we’ll embark on a long shuttle ride back to the host hotel in Columbia, TN.