| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $11,813.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $6,400.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $9,600.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $6,500.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $6,040.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $5,800.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $0.00 | PMC Rider |
| 2017 | $1,000.00 | PMC Rider |
| 2016 | $7,890.00 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $7,465.00 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $6,900.00 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $7,840.00 | Wellesley to Provincetown Inn (2-Day) |
| 2012 | $6,525.00 | Wellesley to Provincetown Inn (2-Day) |
| 2011 | $4,200.00 | Wellesley to Provincetown Inn (2-Day) |
| 2010 | $4,280.00 | Wellesley to Provincetown Inn (2-Day) |
| 2009 | $4,434.68 | Wellesley to Provincetown Inn (2-Day) |
