| 2025 | $0.00 | PMC Virtual Rider |
| 2024 | $19,479.00 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $11,298.00 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $15,312.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $17,756.00 | Reimagined |
| 2020 | $14,301.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $16,001.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $10,464.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $7,821.21 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $200.00 | PMC Rider |
| 2015 | $9,926.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $8,433.00 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $8,575.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $6,510.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $5,950.00 | Wellesley to Provincetown Inn (2-Day) |
| 2010 | $5,336.67 | Wellesley to Provincetown Inn (2-Day) |
| 2009 | $4,300.00 | Wellesley to Provincetown Inn (2-Day) |
| 2008 | $4,430.00 | Wellesley to Bourne (1-Day, Sat) |
| 1990 | $150.00 | PMC Rider |
