| 2025 | $0.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $8,733.73 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $11,828.10 | Wellesley to Provincetown Monument (2-Day) |
| 2022 | $13,210.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $11,660.00 | Reimagined |
| 2020 | $15,537.10 | Wellesley to Provincetown Inn (2-Day) |
