| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $5,718.16 | Reimagined |
| 2023 | $19,320.13 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $22,908.02 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $14,950.12 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $0.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $34,372.84 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $55,206.13 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $35,375.70 | Bourne to Wellesley (1-Day, Sun) |
