| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $6,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $10,487.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $10,022.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $9,760.00 | Wellesley Century |
| 2020 | $2,660.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $8,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $8,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $7,920.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $7,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $7,450.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $11,350.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $11,250.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $11,432.00 | Wellesley to Wellesley (2-Day) |
| 2011 | $7,733.00 | Sturbridge to Provincetown Inn (2-Day) |
