| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $7,091.62 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $7,165.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $3,055.00 | Reimagined |
| 2021 | $6,460.00 | Reimagined |
| 2020 | $4,810.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $7,582.50 | PMC Virtual Rider and Volunteer |
| 2018 | $6,885.00 | Sturbridge to Provincetown Inn (2-Day) |
