| 2025 | $0.00 | Wellesley to Provincetown Monument (2-Day) |
| 2024 | $10,288.55 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $10,555.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $17,111.11 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $9,250.11 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $0.00 | PMC Rider |
| 2019 | $8,543.33 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $5,711.11 | Sturbridge to Provincetown Inn (2-Day) |
