| 2025 | $0.00 | PMC |
| 2024 | $6,002.06 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $2,315.00 | PMC Unpaved |
| 2022 | $6,149.55 | Sturbridge to Provincetown Monument (2-Day) |
| $1,500.00 | PMC Unpaved | |
| 2021 | $8,000.00 | Reimagined |
| 2020 | $10,018.56 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,523.00 | Sturbridge to Provincetown Inn (2-Day) |
