| Introduction: | heart | 3 |
| Shakedown ride: | heart | 2 |
| Northern Terminus to Fly (Creekview Farm Retreat B&B: | heart | 1 |
| Fly, TN to Collinwood, TN: | heart | 1 |
| Collinwood, TN to Belmont, MS: | heart | 1 |
| Belmont, MS to Houston, MS: | heart | 1 |
| Houston, MS to Kosciusko, MS: | heart | 1 |
| Kosciusko, MS to Clinton, MS: | heart | 1 |
| Belmont, MS to Port Gibson, MS: | heart | 1 |
| Port Gibson, MS to Natchez, MS: | heart | 1 |
| Epilogue | heart | 2 |