| 2023 | $10,920.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $10,711.28 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $9,460.23 | Wellesley to Bourne + Wellesley Century (2-Day) |
| 2020 | $4,182.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $9,610.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $7,424.15 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $10,609.50 | Wellesley to Provincetown Inn (2-Day) |
