| 2024 | $0.00 | PMC |
| 2023 | $6,030.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $6,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $3,180.00 | Reimagined |
| 2020 | $1,650.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $5,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $5,344.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $4,800.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $4,690.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2015 | $7,080.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2014 | $4,300.00 | Wellesley to Provincetown Monument (2-Day) |
| 2013 | $4,300.00 | Wellesley to Provincetown Monument (2-Day) |
| 2012 | $4,300.00 | Wellesley to Provincetown Monument (2-Day) |
| 2011 | $4,910.00 | Wellesley to Provincetown Monument (2-Day) |
