| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $15,013.51 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $16,603.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $16,490.20 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $14,520.00 | Reimagined |
| 2020 | $11,180.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $15,395.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $6,365.00 | Wellesley to Wellesley (2-Day) |
| 2017 | $5,367.50 | Wellesley to Bourne (1-Day, Sat) |
