| 2025 | $0.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $3,435.00 | Reimagined |
| 2023 | $8,566.23 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $7,310.00 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $9,930.00 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $5,795.00 | Wellesley to Bourne (1-Day, Sat) |
| 2019 | $4,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2018 | $5,295.00 | Wellesley to Bourne (1-Day, Sat) |
| 2017 | $4,403.00 | Wellesley to Bourne (1-Day, Sat) |
| 2016 | $5,500.00 | Wellesley to Bourne (1-Day, Sat) |
| 2015 | $5,875.00 | Wellesley to Bourne (1-Day, Sat) |
| 2014 | $6,612.00 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $4,645.00 | Wellesley to Provincetown Inn (2-Day) |
| 2012 | $5,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2011 | $5,450.00 | Wellesley to Provincetown Inn (2-Day) |
| 2010 | $5,109.00 | Wellesley to Provincetown Inn (2-Day) |
