| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $19,458.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $31,691.92 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $17,117.75 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $20,233.75 | Wellesley Century |
| 2020 | $15,876.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $11,362.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $7,751.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $8,432.02 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $5,519.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $7,217.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $4,990.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $4,660.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $4,656.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $4,200.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $8,450.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $8,262.00 | Sturbridge to Provincetown Monument (2-Day) |
