| 2025 | $200.00 | Wellesley to Wellesley (50 mile Sunday) and Volunteer |
| 2024 | $6,528.92 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $3,982.16 | Reimagined |
| 2022 | $6,828.10 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $3,670.18 | Wellesley to Wellesley (50 mile Sunday) |
| 2020 | $4,330.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,969.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $6,825.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $5,834.11 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $4,500.56 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $6,050.00 | Wellesley to Provincetown Monument (2-Day) |
| 2014 | $5,000.00 | Wellesley to Provincetown Monument (2-Day) |
