| 2024 | $11,850.00 | Sturbridge to Provincetown Inn (2-Day) |
| $1,750.00 | PMC Unpaved | |
| 2023 | $6,750.00 | Sturbridge to Provincetown Inn (2-Day) |
| $1,500.00 | PMC Unpaved | |
| 2022 | $10,966.78 | Sturbridge to Provincetown Inn (2-Day) |
| $1,870.00 | PMC Unpaved | |
| 2021 | $7,095.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2020 | $6,125.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $6,895.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $6,050.63 | Wellesley to Bourne (1-Day, Sat) |
