| David Swanson | $50.00 |
| 2025 | $1,550.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $11,102.65 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $5,600.00 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $5,035.00 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $5,060.00 | Reimagined |
| 2020 | $4,820.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $6,523.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $8,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $8,150.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $7,500.00 | Sturbridge to Provincetown Monument (2-Day) |
