| 2022 | $4,801.00 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $2,000.00 | Reimagined |
| 2020 | $1,812.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $5,675.00 | Wellesley to Bourne (1-Day, Sat) |
| 2018 | $5,268.54 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $5,147.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $5,203.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $4,500.29 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $4,400.28 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $4,300.35 | Sturbridge to Provincetown Inn (2-Day) |
