| 2024 | $12,333.62 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $8,395.00 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $7,317.00 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $6,876.88 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $25.00 | PMC Rider |
| 2018 | $0.00 | PMC Rider |
| 2017 | $1,000.00 | PMC Rider |
| 2016 | $5,764.75 | Wellesley to Provincetown Monument (2-Day) |
| 2015 | $6,096.12 | Wellesley to Provincetown Monument (2-Day) |
| 2014 | $4,300.00 | Wellesley to Provincetown Monument (2-Day) |
| 2013 | $4,393.74 | Wellesley to Provincetown Inn (2-Day) |
| 2012 | $3,100.00 | Wellesley to Bourne (1-Day, Sat) |
