| 2025 | $0.00 | PMC Unpaved |
| 2024 | $10,900.80 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $9,370.90 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $12,191.55 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $9,000.00 | Reimagined |
| 2020 | $1,534.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $5,152.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $6,345.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $6,241.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $7,586.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $4,835.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $6,450.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $5,877.21 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $9,085.58 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $6,777.19 | Sturbridge to Provincetown Inn (2-Day) |
