| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $2,500.00 | Reimagined |
| 2023 | $13,038.32 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $12,470.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $3,940.00 | Reimagined |
| 2020 | $2,050.00 | PMC Rider |
| 2019 | $11,916.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $8,125.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $7,940.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $8,398.12 | Wellesley to Provincetown Monument (2-Day) |
