| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $35,450.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $45,915.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $21,461.00 | Reimagined |
| $700.00 | PMC Winter Cycle | |
| 2021 | $26,130.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $24,750.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $8,500.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $4,950.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $7,800.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $10,000.00 | Wellesley to Provincetown Inn (2-Day) |
