| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $10,950.00 | Virtual Ride |
| 2023 | $16,310.00 | Wellesley to Patriot Place (25 mile Sunday) |
| 2022 | $12,400.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $10,010.00 | Reimagined |
| 2020 | $11,127.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $6,330.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $6,317.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $8,132.58 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $8,279.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $7,205.00 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $5,459.89 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $5,831.09 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $5,451.00 | Sturbridge to Provincetown Inn (2-Day) |
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