| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $10,063.43 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $10,260.42 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $16,625.72 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $17,055.62 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $10,430.00 | Sturbridge to Provincetown Inn (2-Day) |
