| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $6,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $10,212.20 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $9,925.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $9,974.00 | Bourne to Provincetown Monument (1-Day, Sun) |
| 2020 | $252.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $8,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $8,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $8,052.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $7,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $7,200.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2014 | $11,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2013 | $6,800.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2012 | $6,530.00 | Wellesley to Provincetown Monument (2-Day) |
