| 2025 | $0.00 | Wellesley to Provincetown Monument (2-Day) |
| 2024 | $17,283.51 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $17,250.16 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $17,301.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $17,894.18 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $16,035.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $15,465.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $19,062.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $22,420.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $18,535.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $19,642.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $20,677.25 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $18,425.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $23,549.75 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $18,530.60 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $18,055.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $18,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $16,450.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $20,130.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $21,975.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $20,085.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $20,260.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $19,855.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2002 | $14,887.72 | Sturbridge to Provincetown Inn (2-Day) |
| 2001 | $12,295.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2000 | $10,205.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1999 | $5,220.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1998 | $2,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1997 | $2,025.00 | PMC Rider |
| 1996 | $1,900.00 | PMC Rider |
| 1995 | $2,855.00 | PMC Rider |
| 1994 | $1,805.00 | PMC Rider |
| 1993 | $0.00 | PMC Rider |
