| 2025 | $0.00 | Reimagined |
| 2024 | $2,164.00 | Reimagined |
| 2023 | $3,278.00 | Wellesley Century |
| 2022 | $5,058.44 | Wellesley Century |
| 2021 | $3,742.77 | Wellesley to Bourne + Wellesley Century (2-Day) |
| 2020 | $5,013.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,355.00 | Sturbridge to Provincetown Inn (2-Day) |
