| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $6,587.30 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $6,105.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $6,198.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $6,000.00 | Sturbridge to Bourne + Wellesley Century (2-Day) |
| 2020 | $2,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,180.00 | Sturbridge to Provincetown Inn (2-Day) |
