| Mark Tauster | $50.00 |
| John Sheather | $50.00 |
| Ralph Steele | $25.00 |
|
Robert F Miller |
|
|
Peter Ryan |
|
| Mark Elliott | $50.00 |
| Joseph Hanley | $100.00 |
|
Kelly Walker |
$150.00 |
| 2025 | $4,205.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $10,001.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $10,052.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $14,360.00 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $795.83 | Virtual Ride |
| 2020 | $3,544.80 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $7,674.20 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $9,241.04 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $9,291.42 | Bourne to Provincetown Inn (1-Day, Sun) |
| 2016 | $9,808.20 | Bourne to Provincetown Inn (1-Day, Sun) |
| 2015 | $4,720.00 | Bourne to Provincetown Inn (1-Day, Sun) |
| 2014 | $3,955.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2013 | $4,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $6,667.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $4,257.00 | Sturbridge to Provincetown Inn (2-Day) |
