| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| $400.00 | PMC Winter Cycle | |
| 2024 | $11,071.47 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $11,062.10 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $11,813.32 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $9,508.40 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $9,310.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $11,885.30 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $9,325.00 | Wellesley to Provincetown Inn (2-Day) |
| 2017 | $6,940.00 | Bourne to Provincetown Inn (1-Day, Sun) |
| 2016 | $5,600.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $6,250.00 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $7,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $6,700.00 | Wellesley to Provincetown Inn (2-Day) |
| 2012 | $7,214.85 | Wellesley to Bourne (1-Day, Sat) |
| 2011 | $7,466.60 | Wellesley to Provincetown Inn (2-Day) |
| 2010 | $8,185.00 | Wellesley to Provincetown Inn (2-Day) |
| 2009 | $8,820.45 | Wellesley to Provincetown Inn (2-Day) |
| 2008 | $9,346.04 | Wellesley to Provincetown Inn (2-Day) |
| 2007 | $10,956.71 | Wellesley to Provincetown Inn (2-Day) |
| 2006 | $9,207.67 | Wellesley to Provincetown Inn (2-Day) |
| 2005 | $12,196.67 | Wellesley to Provincetown Inn (2-Day) |
| 2004 | $7,275.00 | Wellesley to Provincetown Inn (2-Day) |
| 2003 | $6,990.00 | Wellesley to Provincetown Inn (2-Day) |
| 2002 | $4,070.00 | Wellesley to Provincetown Inn (2-Day) |
| 2001 | $4,312.40 | Wellesley to Bourne (1-Day, Sat) |
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