| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $22,079.80 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $6,200.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $5,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $4,875.00 | Wellesley to Bourne (1-Day, Sat) |
