| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $6,135.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $6,018.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $6,180.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $4,725.00 | Wellesley Century |
| 2020 | $40.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $5,100.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $4,800.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $5,005.00 | Sturbridge to Provincetown Inn (2-Day) |
