| 2025 | $480.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $7,825.38 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $6,560.00 | Wellesley Century |
| 2022 | $7,655.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $5,070.00 | Wellesley Century |
| 2020 | $5,595.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $8,126.60 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $8,026.00 | Sturbridge to Provincetown Inn (2-Day) |
