| 2025 | $120.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $21,354.80 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $31,613.24 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $16,632.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $20,838.50 | Bourne to Provincetown Monument (1-Day, Sun) |
| 2020 | $15,055.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $10,360.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $13,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $10,465.33 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $9,101.33 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $8,475.00 | Bourne to Provincetown Monument (1-Day, Sun) |
| 2014 | $8,411.12 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $10,790.00 | Sturbridge to Provincetown Inn (2-Day) |
