| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $21,451.07 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $13,575.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $17,424.69 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $16,241.50 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $3,960.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $8,753.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $9,025.00 | Sturbridge to Provincetown Inn (2-Day) |
| $500.00 | PMC Winter Cycle | |
| 2017 | $12,368.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $7,660.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $8,850.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $7,800.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $10,250.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $10,695.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $10,540.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $7,720.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $4,200.00 | Sturbridge to Provincetown Inn (2-Day) |
