| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $12,940.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $15,035.17 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $7,887.70 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $6,495.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2020 | $5,317.00 | Sturbridge to Bourne (1-Day, Sat) |
