| 2025 | $0.00 | PMC Volunteer |
| 2024 | $0.00 | PMC Volunteer |
| 2023 | $100.00 | PMC Volunteer |
| 2022 | $6,606.41 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $2,166.41 | Reimagined |
| 2020 | $983.69 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $5,016.69 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $6,825.00 | Wellesley to Provincetown Inn (2-Day) |
