| 2025 | $200.00 | PMC Unpaved |
| 2024 | $0.00 | PMC |
| $1,965.00 | PMC Unpaved | |
| 2022 | $7,195.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $3,785.00 | Reimagined |
| 2020 | $2,933.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $8,500.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $4,900.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $4,850.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $4,820.00 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $7,200.00 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $6,900.00 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $3,200.00 | Wellesley to Bourne (1-Day, Sat) |
