| Patricia Barnard | $130.00 |
| 2025 | $3,130.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $4,675.00 | Wellesley Century |
| 2023 | $2,960.00 | Reimagined |
| 2022 | $6,000.00 | Wellesley Century |
| 2021 | $3,400.00 | Wellesley Century |
| 2020 | $2,750.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,110.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $4,944.67 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $4,800.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $4,500.12 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $4,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $4,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $4,480.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $4,200.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $4,200.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $4,200.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $4,000.00 | Sturbridge to Provincetown Inn (2-Day) |
