| Carson Christman | $1,000.00 |
|
Olwen Weatherhead |
| 2025 | $2,200.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $7,493.35 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $6,100.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $3,081.11 | Reimagined |
| 2021 | $4,609.13 | Wellesley Century |
| 2020 | $2,000.00 | Sturbridge to Provincetown Inn (2-Day) |
