| Chase Mckee | $100.00 |
| Michael Crandell | $120.00 |
| Connor McNeill | $300.00 |
|
Patrick Mcfeeley |
$1,000.00 |
| 2025 | $4,020.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $14,153.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $7,706.07 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $14,621.06 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $11,060.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $4,940.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $6,500.00 | Wellesley to Bourne (1-Day, Sat) |
