| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $7,640.39 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $7,700.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $10,938.63 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $6,000.20 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $1,375.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $5,137.50 | Wellesley to Bourne (1-Day, Sat) |
| 2018 | $5,000.00 | Wellesley to Bourne (1-Day, Sat) |
| $250.00 | PMC Winter Cycle | |
| 2017 | $5,575.00 | Wellesley to Bourne (1-Day, Sat) |
| 2016 | $4,200.00 | Wellesley to Bourne (1-Day, Sat) |
| 2015 | $3,900.00 | Wellesley to Bourne (1-Day, Sat) |
| 2014 | $3,200.00 | Wellesley to Bourne (1-Day, Sat) |
| 2013 | $4,450.00 | Wellesley to Bourne (1-Day, Sat) |
| 2012 | $0.00 | PMC Volunteer |
| 2011 | $0.00 | PMC Volunteer |
| 2010 | $0.00 | PMC Volunteer |
