| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $9,558.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $6,880.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $6,120.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $4,000.00 | Wellesley to Bourne (1-Day, Sat) |
