| 2025 | $0.00 | PMC |
| 2024 | $3,420.00 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $6,250.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $6,330.00 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $4,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $79.79 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $5,440.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $4,164.00 | Wellesley to Bourne (1-Day, Sat) |
| 2017 | $4,665.00 | Wellesley to Bourne (1-Day, Sat) |
| $0.00 | The Resolution by PMC | |
| 2016 | $5,025.04 | Wellesley to Bourne (1-Day, Sat) |
