| David Mahaney | $50.00 |
|
John Egan |
$50.00 |
| 2025 | $200.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2024 | $3,830.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2023 | $2,600.00 | Reimagined |
| 2022 | $775.00 | Virtual Ride |
| 2018 | $6,063.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $4,941.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $4,625.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2015 | $7,228.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $7,102.25 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $4,240.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $4,278.00 | Sturbridge to Provincetown Inn (2-Day) |
