| 2025 | $0.00 | PMC |
| 2024 | $44,405.00 | Wellesley to Provincetown Monument (2-Day) |
| 2023 | $52,300.00 | Wellesley to Provincetown Monument (2-Day) |
| 2022 | $41,117.10 | Wellesley to Provincetown Monument (2-Day) |
| 2021 | $36,000.00 | Wellesley to Provincetown Monument (2-Day) and Volunteer |
| 2020 | $25,025.01 | Wellesley to Provincetown Monument (2-Day) |
| 2019 | $22,321.00 | Wellesley to Provincetown Monument (2-Day) |
| 2018 | $27,149.00 | Wellesley to Provincetown Monument (2-Day) |
| 2017 | $19,625.00 | Wellesley to Provincetown Monument (2-Day) |
| 2016 | $22,091.00 | Wellesley to Provincetown Monument (2-Day) |
| 2015 | $16,546.00 | Wellesley to Provincetown Monument (2-Day) |
| 2014 | $13,610.00 | Wellesley to Provincetown Monument (2-Day) |
| 2013 | $11,250.00 | Wellesley to Provincetown Monument (2-Day) |
| 2012 | $12,000.00 | Wellesley to Provincetown Monument (2-Day) |
| 2011 | $8,185.00 | Wellesley to Provincetown Monument (2-Day) |
| 2010 | $6,735.00 | Wellesley to Provincetown Monument (2-Day) |
