| 2025 | $0.00 | Wellesley to Provincetown Monument (2-Day) |
| 2024 | $4,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $9,200.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $9,725.00 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $7,710.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $2,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $9,673.09 | Wellesley to Bourne (1-Day, Sat) |
| 2018 | $21,646.00 | Wellesley to Provincetown Monument (2-Day) |
| 2017 | $22,551.22 | Wellesley to Provincetown Monument (2-Day) |
| 2016 | $44,155.00 | Wellesley to Provincetown Monument (2-Day) |
