| Emmy Grunseich | $500.00 |
| 2025 | $1,500.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $5,825.00 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $4,198.55 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $21,325.00 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $14,083.55 | Sturbridge to Bourne (1-Day, Sat) |
| 2020 | $0.00 | PMC Rider |
| 2019 | $8,600.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $8,044.25 | Sturbridge to Bourne (1-Day, Sat) |
| 2017 | $7,925.00 | Wellesley to Provincetown Monument (2-Day) |
| 2016 | $6,822.50 | Wellesley to Bourne (1-Day, Sat) |
| 2015 | $7,493.18 | Sturbridge to Provincetown Inn (2-Day) |
