| Katie Davis | |
| Bret Purvis | $25.00 |
| Maiju Purvis | $25.00 |
| 2025 | $350.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $32,885.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $33,831.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $29,815.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $41,788.00 | Wellesley Century |
| 2020 | $43,443.88 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $55,282.46 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $38,185.54 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $27,099.73 | Sturbridge to Provincetown Inn (2-Day) |
