| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $10,127.83 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $10,392.13 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $9,512.85 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $9,100.00 | Wellesley to Bourne + Wellesley Century (2-Day) |
| 2020 | $9,035.25 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $9,041.25 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $8,051.25 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $7,950.25 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $7,505.00 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $8,735.41 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $7,192.89 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $7,083.09 | Wellesley to Provincetown Inn (2-Day) |
| 2012 | $6,850.00 | Wellesley to Provincetown Inn (2-Day) |
| 2011 | $5,607.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $4,200.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $4,666.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $5,315.54 | Wellesley to Provincetown Inn (2-Day) |
| 2007 | $4,037.02 | Wellesley to Provincetown Inn (2-Day) |
| 2006 | $3,489.25 | Wellesley to Provincetown Inn (2-Day) |
| 2005 | $3,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2004 | $2,750.00 | Wellesley to Provincetown Inn (2-Day) |
| 2003 | $2,545.25 | Wellesley to Provincetown Inn (2-Day) |
| 2002 | $1,130.00 | Wellesley to Bourne (1-Day, Sat) |
