| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $5,453.53 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $6,850.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $6,030.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $9,475.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $5,055.00 | Sturbridge to Provincetown Inn (2-Day) |
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