| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $10,978.10 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $4,923.10 | Reimagined |
| 2022 | $9,788.68 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $7,185.00 | Wellesley to Bourne (1-Day, Sat) |
| $100.00 | PMC Winter Cycle | |
| 2020 | $5,525.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $8,760.50 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $5,225.00 | Wellesley to Bourne (1-Day, Sat) and Volunteer |
| 2017 | $4,455.00 | Wellesley to Bourne (1-Day, Sat) |
| 2016 | $4,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2015 | $6,065.00 | Wellesley to Provincetown Monument (2-Day) |
