| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $24,775.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $19,538.55 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $21,515.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $23,635.00 | Wellesley Century |
| 2020 | $16,410.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $13,011.13 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $12,812.13 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $9,662.13 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $7,811.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $7,669.12 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $7,690.87 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $7,676.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $8,756.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $5,125.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $5,750.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $4,620.00 | Sturbridge to Provincetown Inn (2-Day) |
