| 2025 | $100.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $11,110.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $13,230.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $13,479.88 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $12,254.27 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $9,452.35 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $10,205.40 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $11,549.11 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $8,351.00 | Wellesley to Provincetown Inn (2-Day) |
