| Coleen Thomsen |
| 2025 | $50.00 | PMC Virtual Rider |
| 2024 | $6,250.00 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $6,365.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $22,337.75 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $19,704.00 | Reimagined |
| 2020 | $16,823.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $14,852.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $14,786.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $13,486.69 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $2,600.00 | PMC Rider |
| 2015 | $14,158.00 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $14,352.00 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $13,231.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $14,575.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $10,980.00 | Wellesley to Provincetown Inn (2-Day) |
| 2010 | $11,385.00 | Wellesley to Provincetown Inn (2-Day) |
| 2009 | $9,530.00 | Wellesley to Provincetown Inn (2-Day) |
| 2008 | $7,849.00 | Wellesley to Provincetown Inn (2-Day) |
| 2007 | $8,662.00 | Wellesley to Provincetown Monument (2-Day) |
| 1999 | $1,993.13 | Sturbridge to Bourne (1-Day, Sat) |
| 1998 | $2,884.00 | Sturbridge to Provincetown Inn (2-Day) |
