| 2025 | $1,600.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $17,084.71 | Sturbridge to Provincetown Inn (2-Day) |
| $1,550.00 | PMC Unpaved | |
| 2023 | $13,474.00 | Sturbridge to Provincetown Inn (2-Day) |
| $1,500.00 | PMC Unpaved | |
| 2022 | $11,782.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $11,298.80 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $11,246.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $11,385.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $10,575.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $6,340.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $6,627.40 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $5,220.00 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $4,339.00 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $6,786.00 | Wellesley to Provincetown Inn (2-Day) |
| 2012 | $4,428.00 | Wellesley to Provincetown Inn (2-Day) |
| 2011 | $4,514.00 | Wellesley to Provincetown Inn (2-Day) |
| 2010 | $6,519.00 | Wellesley to Provincetown Inn (2-Day) |
| 2009 | $7,703.00 | Wellesley to Provincetown Inn (2-Day) |
