| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $10,083.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $10,629.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $13,296.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $9,692.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $7,651.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $15,272.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $13,873.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $10,001.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $8,217.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $8,781.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2014 | $8,312.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2013 | $8,481.18 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $7,224.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2011 | $6,860.20 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $7,260.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2009 | $5,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2008 | $5,041.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $5,197.00 | Sturbridge to Provincetown Monument (2-Day) |
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