| 2024 | $4,203.00 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $6,015.00 | Bourne to Provincetown Monument (1-Day, Sun) |
| 2022 | $6,025.00 | Reimagined |
| 2021 | $4,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $50.00 | Wellesley to Bourne (1-Day, Sat) |
| 2019 | $4,009.93 | Wellesley to Bourne (1-Day, Sat) |
| 2018 | $4,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2017 | $4,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2016 | $3,700.00 | Wellesley to Bourne (1-Day, Sat) |
| 2015 | $3,400.00 | Wellesley to Bourne (1-Day, Sat) |
| 2014 | $4,796.25 | Wellesley to Bourne (1-Day, Sat) |
| 2013 | $3,200.00 | Wellesley to Bourne (1-Day, Sat) |
| 2012 | $3,104.00 | Wellesley to Bourne (1-Day, Sat) |
| 2011 | $3,003.00 | Wellesley to Bourne (1-Day, Sat) |
