| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $14,337.06 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $9,156.30 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $9,825.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $6,486.07 | Wellesley Century |
| 2020 | $11,020.32 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $10,534.92 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $10,275.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $10,350.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $11,650.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $7,366.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $9,345.62 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $12,319.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $10,013.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $8,597.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $6,905.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $5,745.00 | Sturbridge to Provincetown Inn (2-Day) |
