| 2025 | $103.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $8,590.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $10,243.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $6,600.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $5,950.00 | Wellesley Century |
| 2020 | $2,660.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $11,686.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $8,025.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $7,825.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $6,855.00 | Bourne to Provincetown Inn (1-Day, Sun) |
