| 2024 | $5,260.00 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $5,365.00 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $6,340.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $3,025.00 | Wellesley Century |
| 2020 | $4,565.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $6,845.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $8,639.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $7,075.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $7,625.00 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $8,250.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $7,700.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $6,620.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $5,800.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $5,713.32 | Sturbridge to Bourne (1-Day, Sat) |
| 2010 | $4,707.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $3,050.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2008 | $3,270.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2007 | $2,945.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2006 | $3,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $2,000.00 | Wellesley to Bourne (1-Day, Sat) |
