| Joseph Buchheit | $5,000.00 |
| 2025 | $5,000.00 | PMC Fundraiser |
| 2024 | $14,289.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $14,019.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $7,699.05 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $7,350.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $10,359.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $10,729.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $11,619.45 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $18,294.53 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $26,290.93 | Sturbridge to Bourne (1-Day, Sat) |
