| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $10,050.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $10,001.69 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $11,600.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $11,255.00 | Reimagined |
| 2020 | $9,180.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $8,519.10 | Wellesley to Provincetown Inn (2-Day) |
| $1,250.00 | PMC Winter Cycle | |
| 2018 | $8,000.00 | Wellesley to Wellesley (2-Day) |
| $1,100.00 | PMC Winter Cycle | |
| 2017 | $5,525.00 | Wellesley to Bourne (1-Day, Sat) |
