| 2025 | $500.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $34,740.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $28,280.00 | Wellesley to Provincetown Monument (2-Day) |
| 2022 | $53,646.00 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $48,760.00 | Wellesley Century |
| 2020 | $8,880.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $36,963.00 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $18,944.29 | Wellesley to Provincetown Monument (2-Day) |
| 2017 | $34,192.22 | Wellesley to Provincetown Monument (2-Day) |
| 2016 | $46,495.50 | Wellesley to Provincetown Monument (2-Day) |
