| 2025 | $125.00 | Wellesley to Provincetown Monument (2-Day) |
| 2024 | $16,761.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2023 | $18,686.20 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $16,921.20 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $15,533.20 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $14,947.60 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $20,570.33 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $31,515.06 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $16,203.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2016 | $25,667.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2015 | $36,957.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2014 | $49,036.32 | Sturbridge to Provincetown Monument (2-Day) |
| 2013 | $45,108.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2012 | $48,654.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2011 | $49,088.88 | Sturbridge to Provincetown Monument (2-Day) |
| 2010 | $38,195.99 | Sturbridge to Provincetown Monument (2-Day) |
| 2009 | $46,468.64 | Sturbridge to Provincetown Monument (2-Day) |
| 2008 | $54,002.51 | Sturbridge to Provincetown Monument (2-Day) |
| 2007 | $58,395.07 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $34,324.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2005 | $46,519.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $29,590.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $28,658.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2002 | $31,254.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2001 | $26,930.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2000 | $27,164.50 | Sturbridge to Provincetown Inn (2-Day) |
| 1999 | $10,892.00 | Sturbridge to Provincetown Inn (2-Day) |
