| Todd Tierney | $75.00 |
| 2025 | $575.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $18,750.74 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $23,545.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $16,498.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $20,320.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $15,885.15 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $13,505.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $14,533.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $7,838.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $13,108.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $13,384.69 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $9,507.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $6,803.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $4,370.00 | Wellesley to Wellesley (50 mile Sunday) |
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