| 2024 | $260.00 | PMC Volunteer |
| 2023 | $10,050.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $12,322.29 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $9,120.20 | Reimagined |
| 2020 | $12,878.30 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $18,891.11 | Sturbridge to Provincetown Inn (2-Day) |
