| 2023 | $0.00 | PMC Volunteer |
| 2022 | $9,500.00 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $9,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $9,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $5,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $8,000.00 | Wellesley to Provincetown Inn (2-Day) |
