| 2025 | $100.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $48,691.09 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $41,822.39 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $33,317.02 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $24,600.94 | Reimagined |
| 2020 | $20,980.75 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $26,487.21 | Sturbridge to Bourne (1-Day, Sat) |
