| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $12,015.27 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $10,296.11 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $15,562.22 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $12,101.11 | Wellesley to Bourne + Wellesley Century (2-Day) |
| 2020 | $5,866.11 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $9,201.11 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $8,932.65 | Sturbridge to Provincetown Inn (2-Day) |
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