| 2025 | $0.00 | PMC |
| 2024 | $6,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $0.00 | PMC Volunteer |
| 2022 | $6,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $6,055.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $9,901.54 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $5,000.00 | Wellesley to Provincetown Monument (2-Day) |
