| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| $400.00 | PMC Winter Cycle | |
| 2024 | $6,050.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $6,288.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $6,576.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $5,993.39 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $5,167.80 | Wellesley to Bourne (1-Day, Sat) |
