| 2025 | $0.00 | PMC Unpaved |
| 2023 | $9,121.85 | Reimagined |
| 2022 | $16,116.71 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $9,211.23 | Reimagined |
| 2020 | $10,322.13 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $13,658.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $11,550.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $14,432.46 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $32,394.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $15,320.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $26,352.05 | Sturbridge to Provincetown Inn (2-Day) |
