| 2025 | $0.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $22,917.82 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $18,877.00 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $14,453.05 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $12,097.33 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $7,679.00 | Wellesley to Bourne (1-Day, Sat) |
| 2019 | $14,277.00 | Wellesley to Bourne (1-Day, Sat) |
| 2018 | $16,015.00 | Wellesley to Bourne (1-Day, Sat) |
| 2017 | $12,145.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2016 | $9,182.00 | Wellesley to Bourne (1-Day, Sat) |
| 2015 | $10,528.34 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $11,093.87 | Wellesley to Bourne (1-Day, Sat) |
| 2013 | $7,003.00 | Wellesley to Bourne (1-Day, Sat) |
| 2012 | $11,353.33 | Wellesley to Provincetown Inn (2-Day) |
| 2011 | $12,395.34 | Wellesley to Provincetown Inn (2-Day) |
| 2010 | $8,900.00 | Wellesley to Bourne (1-Day, Sat) |
