| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $10,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $8,430.00 | Sturbridge to Provincetown Inn (2-Day) |
| $4,000.00 | PMC Unpaved | |
| 2022 | $8,000.18 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $7,210.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $4,400.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $5,730.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $6,870.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $5,800.00 | Wellesley to Provincetown Monument (2-Day) |
| 2016 | $5,335.00 | Sturbridge to Provincetown Monument (2-Day) |
