| Tina Vandersteel | $550.00 |
| 2025 | $1,100.00 | Wellesley to Provincetown Monument (2-Day) |
| 2024 | $12,461.62 | Wellesley to Provincetown Monument (2-Day) |
| $250.00 | PMC Unpaved | |
| $500.00 | PMC Winter Cycle | |
| 2023 | $11,399.42 | Wellesley to Provincetown Monument (2-Day) |
| 2022 | $12,537.42 | Wellesley to Provincetown Monument (2-Day) |
| $1,500.00 | PMC Unpaved | |
| 2021 | $11,801.00 | Reimagined |
| 2020 | $9,025.00 | Wellesley to Provincetown Monument (2-Day) |
| $500.00 | PMC Winter Cycle | |
| 2019 | $10,407.42 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $8,192.42 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $7,920.42 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $7,972.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2015 | $10,347.04 | Sturbridge to Provincetown Monument (2-Day) |
| 2014 | $7,946.32 | Sturbridge to Provincetown Monument (2-Day) |
| 2013 | $7,625.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2012 | $7,862.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2011 | $7,025.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2010 | $7,789.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2009 | $6,377.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2008 | $6,882.99 | Sturbridge to Provincetown Monument (2-Day) |
| 2007 | $8,215.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2006 | $4,525.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2002 | $2,302.00 | Wellesley to Wellesley (2-Day) |
