| 2025 | $0.00 | Bourne to Provincetown Monument (1-Day, Sun) |
| 2024 | $14,623.18 | Bourne to Provincetown Inn (1-Day, Sun) |
| 2023 | $10,111.11 | Bourne to Provincetown Monument (1-Day, Sun) |
| 2022 | $11,261.11 | Reimagined |
| 2021 | $7,156.60 | Reimagined |
| 2020 | $6,735.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $250.00 | PMC Fundraiser |
