| Jennifer Buras | $100.00 |
| Carly Crockett | |
|
Anonymous |
$51.00 |
| 2025 | $451.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $6,658.33 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $10,000.33 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $9,525.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $10,214.24 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $2,765.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $5,575.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $5,775.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $7,825.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $4,920.00 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $5,475.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $4,955.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $4,800.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $4,550.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $6,408.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $3,505.00 | Sturbridge to Bourne (1-Day, Sat) |
