| James Quinn |
| 2025 | $50.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $10,210.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $17,980.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $16,133.06 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $12,660.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $10,175.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $11,270.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $5,954.01 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $5,346.02 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $8,075.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $5,550.00 | Sturbridge to Provincetown Monument (2-Day) |
