| 2024 | $4,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $6,048.55 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $6,048.55 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $6,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $3,278.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,804.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $8,284.45 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $9,142.90 | Wellesley to Provincetown Inn (2-Day) |
