| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $6,610.43 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $6,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $4,538.00 | Reimagined |
| 2020 | $2,516.41 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $4,800.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $3,920.00 | Wellesley to Bourne (1-Day, Sat) |
| 2013 | $1,585.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2011 | $1,820.00 | Wellesley to Wellesley (50 mile Sunday) |
