| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $16,823.50 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $20,210.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $15,748.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $4,180.00 | Reimagined |
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