| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $10,130.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $9,250.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $7,462.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $8,482.00 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $0.00 | Wellesley to Provincetown Monument (2-Day) |
