| 2025 | $50.00 | Wellesley to Provincetown Monument (2-Day) |
| 2024 | $6,150.00 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $6,600.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2022 | $6,856.00 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $4,695.00 | Reimagined |
| 2020 | $4,400.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $6,870.00 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $7,248.00 | Wellesley to Provincetown Monument (2-Day) |
| 2017 | $6,581.00 | Wellesley to Provincetown Monument (2-Day) |
| 2016 | $5,996.00 | Wellesley to Provincetown Monument (2-Day) |
| 2015 | $4,714.02 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $4,799.89 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $5,467.09 | Wellesley to Provincetown Inn (2-Day) |
| 2012 | $4,319.00 | Wellesley to Provincetown Inn (2-Day) |
| 2011 | $4,239.00 | Wellesley to Provincetown Inn (2-Day) |
| 2010 | $3,266.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2009 | $3,269.00 | Wellesley to Bourne (1-Day, Sat) |
| 2008 | $4,183.00 | Wellesley to Provincetown Inn (2-Day) |
| 2007 | $3,781.00 | Wellesley to Provincetown Inn (2-Day) |
| 2006 | $3,098.70 | Wellesley to Wellesley (2-Day) |
| 2005 | $3,260.00 | Wellesley to Provincetown Inn (2-Day) |
| 2004 | $2,680.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2003 | $1,840.00 | Wellesley to Bourne (1-Day, Sat) |
| 2001 | $900.00 | Wellesley to Bourne (1-Day, Sat) |
