| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $10,108.58 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $10,448.77 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $15,560.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $2,025.00 | Reimagined |
| 2020 | $19,990.40 | Sturbridge to Provincetown Inn (2-Day) |
| $350.81 | PMC Winter Cycle | |
| 2019 | $10,182.25 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $9,150.43 | Sturbridge to Provincetown Monument (2-Day) |
