| 2024 | $6,225.00 | Virtual Ride |
| 2023 | $5,100.00 | Virtual Ride |
| 2022 | $9,500.00 | Reimagined |
| 2021 | $10,010.00 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $9,565.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $13,000.69 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $11,569.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $9,241.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $8,235.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $8,592.27 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $11,875.00 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $12,822.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $7,486.00 | Wellesley to Provincetown Inn (2-Day) |
| 2011 | $9,360.00 | Wellesley to Provincetown Inn (2-Day) |
