| 2025 | $1,600.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $8,594.16 | Wellesley to Provincetown Monument (2-Day) |
| 2022 | $6,421.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $10,526.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $2,550.00 | PMC Rider |
| 2019 | $50.00 | PMC Fundraiser |
| 2018 | $6,336.00 | Sturbridge to Wellesley (2-Day) |
| 2017 | $3,560.00 | Wellesley to Wellesley Teens (50 mile Sunday) |
| 2016 | $3,183.33 | Wellesley to Wellesley Teens (50 mile Sunday) |
