| Marybeth OConnor | $50.00 |
|
Sherry Klein |
| 2025 | $150.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2024 | $5,222.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2023 | $3,522.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2022 | $6,228.00 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $6,750.00 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $125.00 | Wellesley to Bourne (1-Day, Sat) |
| 2019 | $6,500.00 | Wellesley to Bourne (1-Day, Sat) |
| 2018 | $5,229.00 | Wellesley to Bourne (1-Day, Sat) |
| 2017 | $3,577.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2016 | $3,725.00 | Wellesley to Bourne (1-Day, Sat) |
| 2015 | $2,985.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2014 | $4,067.00 | Wellesley to Bourne (1-Day, Sat) |
| 2013 | $3,200.00 | Wellesley to Bourne (1-Day, Sat) |
| 2012 | $4,300.00 | Wellesley to Provincetown Monument (2-Day) |
| 2011 | $2,499.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2010 | $4,676.00 | Wellesley to Provincetown Monument (2-Day) |
| 2009 | $4,200.00 | Wellesley to Provincetown Monument (2-Day) |
| 2007 | $1,654.00 | Wellesley to Wellesley (50 mile Sunday) |
