| 2025 | $0.00 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $8,486.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $8,767.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $8,056.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $75.00 | Sturbridge to Provincetown Inn (2-Day) |
