| 2025 | $0.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $10,023.79 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $10,062.00 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $9,766.00 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $9,196.00 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $12,999.00 | Wellesley to Bourne (1-Day, Sat) |
| 2019 | $8,775.00 | Wellesley to Bourne (1-Day, Sat) |
| 2018 | $8,446.86 | Wellesley to Bourne (1-Day, Sat) |
| 2017 | $7,950.00 | Wellesley to Bourne (1-Day, Sat) |
| 2016 | $7,630.62 | Wellesley to Bourne (1-Day, Sat) |
| 2015 | $7,416.00 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $7,022.00 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $7,083.00 | Wellesley to Bourne (1-Day, Sat) |
| 2012 | $6,511.00 | Wellesley to Provincetown Inn (2-Day) |
| 2011 | $6,690.00 | Wellesley to Provincetown Inn (2-Day) |
| 2010 | $6,387.00 | Wellesley to Bourne (1-Day, Sat) |
