| 2025 | $0.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $36,020.00 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $29,633.55 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $22,113.53 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $18,419.88 | Wellesley Century |
| 2020 | $16,006.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $16,570.50 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $14,232.33 | Wellesley to Provincetown Monument (2-Day) |
| 2017 | $13,023.98 | Wellesley to Provincetown Monument (2-Day) |
| 2016 | $7,789.88 | Wellesley to Provincetown Monument (2-Day) |
| 2015 | $7,320.22 | Wellesley to Provincetown Monument (2-Day) |
| 2014 | $4,793.88 | Wellesley to Provincetown Monument (2-Day) |
| 2013 | $5,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2012 | $6,615.00 | Wellesley to Provincetown Inn (2-Day) |
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