| 2023 | $50.00 | Virtual Ride |
| 2022 | $6,228.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $0.00 | Virtual Ride |
| 2020 | $2,400.00 | PMC Rider |
| 2019 | $10,221.10 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $11,345.45 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $12,117.90 | Wellesley to Provincetown Inn (2-Day) |
