| 2025 | $0.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $6,920.00 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $5,325.00 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $6,223.00 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $7,080.00 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $1,765.00 | PMC Rider |
| 2019 | $100.00 | PMC Fundraiser |
| 2018 | $5,335.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $5,250.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $6,045.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $0.00 | PMC Rider |
| 2013 | $50.00 | PMC Rider |
| 2012 | $4,425.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $125.00 | PMC Rider |
| 2010 | $4,265.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $4,200.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $1,685.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $4,640.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2006 | $4,075.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $3,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $2,750.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2003 | $2,765.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2002 | $2,230.00 | Sturbridge to Provincetown Inn (2-Day) |
