| Jill McGaffigan | $250.00 |
| Derek Doherty | $50.00 |
| 2025 | $300.00 | Reimagined |
| 2024 | $22,697.10 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $20,010.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $32,960.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $22,760.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $25,390.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $33,332.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $30,692.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $27,131.13 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $24,498.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $28,392.25 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $27,432.25 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $17,390.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $14,775.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $14,175.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2010 | $9,140.00 | Wellesley to Bourne (1-Day, Sat) |
