| 2025 | $0.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2024 | $8,375.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $12,347.20 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $11,050.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $6,325.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $5,470.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $9,800.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $13,110.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $11,027.25 | Wellesley to Provincetown Inn (2-Day) |
