| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $10,513.25 | Sturbridge to Provincetown Monument (2-Day) |
| $810.00 | PMC Winter Cycle | |
| 2023 | $14,895.70 | Wellesley to Provincetown Inn (2-Day) |
| $500.00 | PMC Winter Cycle | |
| 2022 | $14,320.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $11,030.00 | Reimagined |
| 2020 | $9,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $8,580.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $5,776.73 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $6,710.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $5,780.00 | Sturbridge to Provincetown Inn (2-Day) |
