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 Add-On Package extends your ride.  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 early 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 two-night stay at Isabella Bed & Breakfast. After checking in, we’ll visit 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 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 back to Isabella Bed & Breakfast to conclude the day. 

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