| 2024 | $250.00 | PMC Volunteer |
| 2023 | $0.00 | PMC Volunteer |
| 2022 | $6,775.00 | Bourne to Provincetown Monument (1-Day, Sun) |
| 2021 | $10,000.00 | Bourne to Provincetown Monument (1-Day, Sun) |
| 2020 | $5,950.00 | Wellesley to Bourne (1-Day, Sat) |
| 2019 | $4,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2018 | $4,250.00 | Wellesley to Bourne (1-Day, Sat) |
| 2017 | $4,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2016 | $3,704.00 | Wellesley to Bourne (1-Day, Sat) |
