| Jennifer Nolan | $120.00 |
| 2025 | $1,920.00 | Wellesley to Provincetown Inn (2-Day) and Volunteer |
| 2024 | $6,370.50 | Wellesley to Provincetown Inn (2-Day) and Volunteer |
| $4,000.00 | PMC Unpaved | |
| 2023 | $10,000.00 | Wellesley to Provincetown Inn (2-Day) and Volunteer |
| 2022 | $9,500.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $9,000.00 | Reimagined and Volunteer |
| 2020 | $9,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $8,700.00 | Wellesley to Provincetown Inn (2-Day) and Volunteer |
| 2018 | $11,458.02 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $7,800.77 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $11,600.95 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $7,200.18 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $11,000.42 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $10,425.00 | Wellesley to Provincetown Inn (2-Day) |
