| 2025 | $2,000.00 | Bourne to Provincetown Inn (1-Day, Sun) |
| 2024 | $11,475.00 | Bourne to Provincetown Inn (1-Day, Sun) |
| 2023 | $12,838.00 | Bourne to Provincetown Inn (1-Day, Sun) |
| 2022 | $9,518.75 | Bourne to Provincetown Monument (1-Day, Sun) |
| 2021 | $12,387.50 | Bourne to Provincetown Monument (1-Day, Sun) |
| 2020 | $9,217.00 | Bourne to Provincetown Monument (1-Day, Sun) |
| 2019 | $10,434.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2018 | $10,720.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2017 | $11,463.97 | Sturbridge to Bourne (1-Day, Sat) |
| 2016 | $11,280.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2015 | $10,207.25 | Sturbridge to Bourne (1-Day, Sat) |
| 2014 | $8,070.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2013 | $8,775.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2012 | $7,465.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2011 | $5,245.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2010 | $5,087.78 | Sturbridge to Bourne (1-Day, Sat) |
| 2009 | $4,725.00 | Wellesley to Bourne (1-Day, Sat) |
| 2007 | $1,283.50 | Wellesley to Wellesley (50 mile Sunday) |
