| 2023 | $10,133.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $50.00 | PMC Fundraiser |
| 2020 | $0.00 | PMC Rider |
| 2019 | $5,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $8,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $8,052.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $7,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $7,320.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2014 | $11,100.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2013 | $6,800.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2012 | $6,754.00 | Wellesley to Provincetown Monument (2-Day) |
