| 2024 | $20,115.00 | Reimagined |
| 2023 | $25,790.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $21,550.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $19,560.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $9,802.25 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $9,110.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $12,669.75 | Wellesley to Provincetown Inn (2-Day) |
