| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $11,227.75 | Sturbridge to Provincetown Monument (2-Day) |
| 2023 | $12,266.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $11,065.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $12,400.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $5,350.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $11,415.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $13,780.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $11,901.13 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $9,681.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2015 | $14,305.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $15,423.38 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $7,143.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2012 | $10,245.00 | Sturbridge to Provincetown Monument (2-Day) |
