| 2025 | $250.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $10,260.00 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $10,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2022 | $8,767.30 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $2,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $25.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $6,787.17 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $7,043.38 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $8,147.04 | Wellesley to Provincetown Inn (2-Day) |
