| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $10,474.16 | Wellesley to Provincetown Inn (2-Day) |
| $4,000.00 | PMC Unpaved | |
| 2023 | $11,988.00 | Sturbridge to Provincetown Inn (2-Day) |
| $1,750.00 | PMC Unpaved | |
| 2022 | $10,671.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $10,822.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $12,350.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $13,600.01 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $12,137.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $10,263.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $10,525.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $9,955.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $11,615.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $10,290.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $8,243.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $7,375.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $5,715.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $6,005.00 | Sturbridge to Provincetown Inn (2-Day) |
