| 2025 | $0.00 | Wellesley to Bourne (1-Day, Sat) and Volunteer |
| 2024 | $20,750.00 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $6,000.00 | Reimagined |
| 2022 | $11,731.00 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $12,575.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $290.00 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $9,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $8,800.00 | Wellesley to Provincetown Monument (2-Day) |
| 2017 | $9,947.22 | Wellesley to Provincetown Monument (2-Day) |
| 2016 | $6,080.00 | Wellesley to Provincetown Monument (2-Day) |
