| 2022 | $6,025.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $3,150.00 | Wellesley Century |
| 2020 | $4,040.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $5,015.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $4,900.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $5,175.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $4,750.00 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $4,500.00 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $4,300.00 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $4,300.00 | Wellesley to Provincetown Inn (2-Day) |
| 2012 | $4,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $4,200.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $4,200.50 | Wellesley to Provincetown Inn (2-Day) |
| 2009 | $5,652.05 | Wellesley to Provincetown Inn (2-Day) |
| 2008 | $4,100.00 | Wellesley to Provincetown Inn (2-Day) |
| 2007 | $3,600.00 | Wellesley to Provincetown Inn (2-Day) |
