| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $6,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $6,100.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $9,530.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $5,436.00 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $7,485.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $10,408.70 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $8,025.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $4,850.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $4,546.12 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $7,300.00 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $6,950.00 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $3,504.00 | Wellesley to Bourne (1-Day, Sat) |
