| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $10,000.11 | Bourne to Provincetown Inn (1-Day, Sun) |
| 2023 | $11,885.93 | Bourne to Provincetown Inn (1-Day, Sun) |
| 2022 | $9,546.11 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $9,415.00 | Wellesley Century |
| 2019 | $11,406.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $9,417.00 | Bourne to Provincetown Inn (1-Day, Sun) |
