| David Krakauer | |
| Jason Breslau | $75.00 |
| 2025 | $2,225.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $10,113.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $13,344.22 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $11,231.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $9,000.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2020 | $7,263.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $10,307.63 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $9,056.00 | Sturbridge to Wellesley (2-Day) |
| 2017 | $7,950.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $7,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $7,201.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $4,467.00 | Sturbridge to Provincetown Inn (2-Day) |
