| Joseph AND Sandra Smith |
| 2025 | $50.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $18,090.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $22,640.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $15,551.00 | Sturbridge to Provincetown Inn (2-Day) |
| $775.60 | PMC Winter Cycle | |
| 2021 | $12,990.00 | Wellesley Century |
| $6,187.50 | PMC Winter Cycle | |
| 2020 | $260.00 | Sturbridge to Provincetown Inn (2-Day) |
| $780.00 | PMC Winter Cycle | |
| 2019 | $8,510.00 | Sturbridge to Provincetown Inn (2-Day) |
| $3,445.00 | PMC Winter Cycle | |
| 2018 | $5,350.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $5,050.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $4,415.00 | Sturbridge to Wellesley (2-Day) |
| 2015 | $4,725.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $4,000.00 | Sturbridge to Wellesley (2-Day) |
| 2013 | $5,400.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2012 | $3,700.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2011 | $3,880.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2010 | $4,311.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2009 | $3,100.00 | Wellesley to Bourne (1-Day, Sat) |
| 2008 | $1,350.00 | Wellesley to Wellesley (50 mile Sunday) |
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