| 2025 | $97.10 | PMC Volunteer |
| 2024 | $10,909.11 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $8,945.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $6,941.38 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $2,360.00 | Reimagined |
| 2020 | $1,275.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $8,559.20 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $5,790.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $7,986.03 | Sturbridge to Bourne (1-Day, Sat) |
| 2016 | $5,403.10 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $5,078.37 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $8,005.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $4,395.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $4,430.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $4,280.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $4,855.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $6,360.00 | Sturbridge to Provincetown Monument (2-Day) |
