| 2023 | $4,666.52 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $100.00 | PMC Fundraiser |
| 2021 | $3,040.00 | Wellesley Century |
| 2020 | $5,992.25 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $6,190.75 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $4,900.00 | Wellesley to Provincetown Monument (2-Day) |
| 2017 | $4,850.00 | Wellesley to Provincetown Monument (2-Day) |
| 2016 | $4,555.12 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $4,617.24 | Wellesley to Provincetown Monument (2-Day) |
