| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $7,075.00 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $6,555.00 | Wellesley to Provincetown Monument (2-Day) |
| 2022 | $6,445.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $3,140.00 | Wellesley Century |
| 2020 | $1,000.00 | Sturbridge to Provincetown Monument (2-Day) |
