| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $14,905.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $13,005.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $9,675.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $13,945.00 | Wellesley Century |
| 2020 | $8,520.01 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $9,272.70 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $7,700.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $11,900.00 | Wellesley to Provincetown Inn (2-Day) |
