| 2023 | $2,530.00 | Reimagined |
| 2022 | $5,675.00 | Reimagined |
| 2021 | $3,000.00 | Wellesley Century |
| 2020 | $2,000.80 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $6,750.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $7,292.88 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $7,859.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $5,304.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $5,477.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $5,075.75 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $4,560.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $4,404.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $4,350.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $3,035.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2003 | $3,305.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2002 | $2,102.00 | Sturbridge to Provincetown Inn (2-Day) |
