| Barbara Cevallos | |
| Thomas Donnelly |
| 2025 | $6,450.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $15,040.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $12,343.33 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $11,263.10 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $12,565.00 | Wellesley Century |
| 2020 | $9,245.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $8,755.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $6,740.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $6,050.00 | Sturbridge to Provincetown Inn (2-Day) |
