| 2024 | $2,071.00 | Reimagined and Volunteer |
| 2023 | $10,310.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $9,500.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $9,225.00 | Reimagined |
| 2020 | $9,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $8,570.00 | Wellesley to Provincetown Inn (2-Day) and Volunteer |
| 2018 | $8,100.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $7,800.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $7,600.00 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $7,200.00 | Wellesley to Bourne (1-Day, Sat) |
| 2014 | $0.00 | PMC Volunteer |
| 2013 | $0.00 | PMC Volunteer |
