| 2025 | $200.00 | Reimagined |
| 2024 | $7,804.18 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $6,026.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $8,832.00 | Reimagined |
| 2021 | $9,470.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $12,650.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $8,503.00 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $5,219.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $8,068.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $5,131.00 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $5,764.00 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $5,940.00 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $5,506.00 | Wellesley to Provincetown Inn (2-Day) |
| 2012 | $5,525.00 | Wellesley to Provincetown Inn (2-Day) |
| 2011 | $4,509.00 | Wellesley to Provincetown Inn (2-Day) |
| 2010 | $4,200.00 | Wellesley to Provincetown Inn (2-Day) |
| 2009 | $4,200.00 | Wellesley to Provincetown Inn (2-Day) |
| 2008 | $4,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2006 | $3,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $3,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $2,710.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2002 | $4,010.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2000 | $1,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1998 | $1,225.00 | Wellesley to Provincetown Inn (2-Day) |
| 1997 | $515.00 | PMC Rider |
