| 2025 | $0.00 | Wellesley to Provincetown Monument (2-Day) |
| 2024 | $11,283.90 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $10,782.80 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $11,934.20 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $12,793.05 | Wellesley Century |
| 2020 | $10,122.74 | Wellesley to Bourne (1-Day, Sat) |
| 2019 | $5,691.00 | Sturbridge to Provincetown Inn (2-Day) |
