| Becky McNiven | $50.00 |
| 2025 | $50.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $11,350.87 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $10,576.16 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $12,123.82 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $12,498.38 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $5,268.56 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $9,660.60 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $9,660.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $8,950.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $9,126.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $6,196.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $11,450.72 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $10,123.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $8,245.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $8,138.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $7,145.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $5,555.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $4,155.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $4,800.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $6,685.00 | Sturbridge to Provincetown Monument (2-Day) |
