| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $8,651.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $8,555.00 | Sturbridge to Provincetown Inn (2-Day) |
| $0.00 | PMC Winter Cycle | |
| 2021 | $9,550.00 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $4,478.40 | Sturbridge to Provincetown Inn (2-Day) |
| $0.00 | PMC Winter Cycle | |
| 2019 | $8,500.60 | Sturbridge to Provincetown Inn (2-Day) |
| $250.00 | PMC Winter Cycle | |
| 2018 | $4,925.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $5,644.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $4,870.00 | Sturbridge to Provincetown Inn (2-Day) |
