| Robert Corbett | $250.00 |
| 2025 | $250.00 | PMC Virtual Rider |
| 2024 | $805.00 | Virtual Ride |
| 2023 | $6,050.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $6,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $4,045.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2020 | $1,365.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,050.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $6,476.39 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $4,800.00 | Sturbridge to Provincetown Inn (2-Day) |
