| Erin Carr | $50.00 |
| Michael Cantalupa |
| 2025 | $1,650.00 | Virtual Ride |
| 2024 | $10,950.80 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $12,067.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $13,060.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $9,414.68 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $9,013.84 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $8,625.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $9,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $9,852.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $14,066.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $8,986.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $11,640.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $11,257.21 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $9,415.58 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $9,640.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $0.00 | PMC Virtual Rider |
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