| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $6,000.99 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $6,195.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $6,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $3,050.00 | Wellesley Century |
| 2020 | $1,780.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $8,500.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $4,900.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $7,800.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $5,145.12 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $5,099.37 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $4,596.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $4,375.08 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $4,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $4,279.96 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $4,246.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $4,490.45 | Sturbridge to Provincetown Inn (2-Day) |
