| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $10,120.30 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $10,015.37 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $6,065.88 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $11,120.29 | Wellesley Century |
| 2020 | $5,664.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $15,700.73 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $5,140.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $5,935.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $4,701.00 | Wellesley to Provincetown Inn (2-Day) |
