| 2024 | $0.00 | PMC |
| 2023 | $7,160.00 | Bourne to Provincetown Inn (1-Day, Sun) |
| 2022 | $8,100.00 | Bourne to Provincetown Monument (1-Day, Sun) |
| 2021 | $6,250.00 | Wellesley to Bourne (1-Day, Sat) |
| 2019 | $8,035.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $6,585.80 | Wellesley to Provincetown Inn (2-Day) |
