| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $9,122.20 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $10,532.45 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $6,242.03 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $5,246.23 | Wellesley Century |
| 2020 | $3,003.23 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $8,901.13 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $8,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $7,920.00 | Wellesley to Provincetown Inn (2-Day) |
