| Pre-Ride Announcement Video | heart | 3 |
| The Box! | heart | 6 |
| My week in Chincoteague | heart | 16 |
| Day 1: Baltimore Airport to Annapolis | heart | 5 |
| Day 2: Annapolis to Washington, DC | heart | 13 |
| Day 3: Washington, DC to Harpers Ferry, WV | heart | 25 |
| Day 4: Harpers Ferry, WV to Hancock, MD | heart | 4 |
| Day 5: Hancock, MD to Frostburg, MD | heart | 14 |
| Day 6: Frostburg, MD to Ohiopyle, PA | heart | 4 |
| Day 7: Ohiopyle, PA to Pittsburgh, PA | heart | 1 |
| Day 8: Rest day in Pittsburgh | heart | 11 |
| Day 9: Pittsburgh, PA to New Castle, PA | heart | 3 |
| Day 10: New Castle, PA to Ravenna, OH | heart | 4 |
| Day 11: Ravenna, OH to Oberlin, OH | heart | 6 |
| Day 12: Oberlin, OH to Fremont, OH | heart | 10 |
| Day 13: Fremont, OH to Defiance, OH | heart | 4 |
| Day 14: Defiance, OH to Huntington, IN | heart | 9 |
| Day 15: Huntington, IN to Rochester, IN | heart | 5 |
| Day 16: Rochester, IN to Valparaiso, IN | heart | 17 |
| Day 17: Valparaiso, IN to Chicago, IL | heart | 3 |
| Wrap up and final thoughts | heart | 2 |