| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $13,257.77 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $12,548.93 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $11,989.01 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $13,696.50 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $7,836.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $7,501.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $8,152.91 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $6,532.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $7,712.45 | Sturbridge to Provincetown Monument (2-Day) |
