| 2025 | $1,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $13,572.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $11,745.18 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $10,750.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $9,127.76 | Sturbridge to Bourne (1-Day, Sat) |
| 2020 | $3,656.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,000.00 | Wellesley to Provincetown Monument (2-Day) |
