| Mark Murphy | $250.00 |
| Francine Flynn |
| 2025 | $300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $13,420.97 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $10,510.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $10,550.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $9,025.25 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $7,666.10 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $7,585.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $2,025.00 | Wellesley to Patriot Place (25 mile Sunday) |
| 2008 | $2,840.00 | Wellesley to Provincetown Inn (2-Day) |
| 2007 | $3,604.29 | Wellesley to Provincetown Inn (2-Day) |
| 2006 | $3,638.00 | Wellesley to Provincetown Inn (2-Day) |
| 2005 | $3,165.00 | Wellesley to Provincetown Inn (2-Day) |
| 2004 | $2,750.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $4,250.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2002 | $4,672.00 | Sturbridge to Wellesley (2-Day) |
