| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $10,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $16,500.00 | Reimagined |
| 2022 | $15,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $22,000.00 | Wellesley Century |
| $1,000.00 | PMC Winter Cycle | |
| 2020 | $9,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $13,996.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $12,525.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $13,850.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $3,700.00 | Wellesley to Bourne (1-Day, Sat) |
