| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $10,067.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $10,125.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $9,525.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $9,627.51 | Wellesley Century |
| 2020 | $75.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,393.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $4,952.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $4,876.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $4,751.06 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $4,510.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $4,505.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $6,700.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $4,500.17 | Sturbridge to Provincetown Inn (2-Day) |
