| Timothy Burke | $1,250.00 |
| 2025 | $1,250.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $14,809.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $18,274.72 | Wellesley to Provincetown Monument (2-Day) |
| 2022 | $24,682.19 | Wellesley to Provincetown Inn (2-Day) |
| $500.00 | PMC Unpaved |
