| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $6,705.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $6,430.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $3,320.00 | Wellesley Century |
| 2020 | $1,730.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,100.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $6,866.13 | Sturbridge to Provincetown Inn (2-Day) |
