| Michael Governale | $50.00 |
| Brittany Totino | $250.00 |
| Samuel Hoffman | $120.00 |
| 2025 | $1,420.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $11,339.91 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $0.00 | PMC Virtual Rider and Volunteer |
| $4,950.00 | PMC Unpaved | |
| 2022 | $9,868.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $9,215.00 | Reimagined |
| 2020 | $5,254.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $8,801.76 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $6,421.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $6,630.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $8,790.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $8,190.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $8,776.12 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $6,813.00 | Sturbridge to Provincetown Inn (2-Day) |
