| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $14,701.17 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $14,108.51 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $13,728.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $14,261.84 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $11,608.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $10,738.69 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $8,696.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $8,253.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $7,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $7,302.00 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $7,007.21 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $6,752.00 | Wellesley to Provincetown Inn (2-Day) |
| 2012 | $6,550.00 | Wellesley to Provincetown Inn (2-Day) |
| 2011 | $6,543.00 | Wellesley to Provincetown Inn (2-Day) |
| 2010 | $5,100.00 | Wellesley to Provincetown Monument (2-Day) |
| 2009 | $6,062.00 | Wellesley to Provincetown Inn (2-Day) |
| 2008 | $6,725.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $9,055.00 | Wellesley to Provincetown Monument (2-Day) |
| 2006 | $9,164.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $8,075.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $11,025.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $8,497.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2002 | $6,687.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2001 | $6,848.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2000 | $6,859.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1999 | $2,666.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1998 | $2,068.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1997 | $1,550.00 | PMC Rider |
