| 2025 | $500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $11,943.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $15,194.20 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $15,518.18 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $11,204.00 | Bourne to Provincetown Monument (1-Day, Sun) |
| 2020 | $30,499.99 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $27,704.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $56,812.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $59,420.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $39,035.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $31,629.74 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $20,266.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $11,607.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $10,225.00 | Wellesley to Provincetown Inn (2-Day) |
| 2011 | $7,528.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $6,518.00 | Sturbridge to Provincetown Inn (2-Day) |
