| Danielle and Mike Tata | $250.00 |
| Danielle and Mike Tata | $15.00 |
| 2025 | $290.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $18,250.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $11,970.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $10,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $9,153.68 | Wellesley Century |
| 2020 | $9,200.00 | Wellesley to Provincetown Inn (2-Day) |
