| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $15,560.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $13,412.42 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $12,604.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $12,700.00 | Sturbridge to Bourne + Wellesley Century (2-Day) |
| 2020 | $2,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,113.00 | Sturbridge to Provincetown Inn (2-Day) |
