| 2025 | $50.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $6,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $6,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $6,120.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $3,000.00 | Wellesley Century |
| 2020 | $2,560.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $5,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $4,900.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $5,300.13 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $3,400.00 | Wellesley to Bourne (1-Day, Sat) |
| 2014 | $4,300.00 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $3,200.00 | Wellesley to Bourne (1-Day, Sat) |
