| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $12,540.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $19,940.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $10,650.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $12,775.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2020 | $40.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,000.00 | Sturbridge to Provincetown Inn (2-Day) |
