| 2024 | $12,838.51 | Sturbridge to Provincetown Inn (2-Day) |
| $400.00 | PMC Winter Cycle | |
| 2023 | $13,540.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $11,163.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $11,580.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2020 | $10,825.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $19,212.86 | Sturbridge to Provincetown Inn (2-Day) |
