| Mark Hollyer | $200.00 |
| 2020 | $260.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $5,359.25 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $5,926.76 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $7,800.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $4,500.50 | Sturbridge to Provincetown Inn (2-Day) |
| 1994 | $1,380.00 | PMC Rider |
| 1993 | $1,042.50 | PMC Rider |
| 1992 | $1,195.00 | PMC Rider |
| 1991 | $1,155.00 | PMC Rider |
| 1990 | $900.00 | PMC Rider |
