| Jim Craige | $250.00 |
| Kathy Lasota | $500.00 |
| Donald Deneen | $100.00 |
| Bronson Kelly | $120.00 |
| 2025 | $970.00 | Reimagined |
| 2024 | $4,725.00 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $6,111.11 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $9,702.10 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $7,325.00 | Wellesley to Provincetown Monument (2-Day) |
