| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $9,435.00 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $10,612.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $4,605.00 | Reimagined |
| 2021 | $4,375.00 | Reimagined |
| 2020 | $4,502.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $200.00 | PMC Rider |
| 2018 | $7,482.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $8,007.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $7,500.45 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $5,077.53 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $5,511.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $4,915.10 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $5,159.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $4,567.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $4,336.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $4,317.00 | Sturbridge to Provincetown Inn (2-Day) |
