| Edward Gee | $50.00 |
| 2025 | $75.00 | Reimagined |
| 2024 | $26,061.18 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $16,728.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $20,600.07 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $15,420.00 | Sturbridge to Provincetown Monument (2-Day) and Volunteer |
| 2020 | $10,265.45 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $10,559.25 | Sturbridge to Provincetown Inn (2-Day) |
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