| 2023 | $4,560.00 | Wellesley to Provincetown Monument (2-Day) |
| 2022 | $6,018.00 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $6,260.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $1,435.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $5,280.00 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $4,100.00 | Bourne to Wellesley (1-Day, Sun) |
