| 2024 | $0.00 | PMC |
| 2023 | $0.00 | PMC Volunteer |
| 2022 | $10,170.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $2,723.00 | Reimagined |
| 2020 | $535.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $0.00 | PMC Volunteer |
| 2018 | $5,295.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $5,050.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $4,950.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $4,600.00 | Wellesley to Provincetown Inn (2-Day) |
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