| 2025 | $0.00 | PMC |
| 2022 | $7,885.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $5,025.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2020 | $4,425.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $6,200.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $7,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $8,610.29 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $8,075.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2015 | $8,070.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2014 | $6,040.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2013 | $6,070.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $5,381.00 | Sturbridge to Bourne (1-Day, Sat) |
