| 2024 | $0.00 | PMC |
| $1,638.51 | PMC Unpaved | |
| 2023 | $2,020.00 | PMC Unpaved |
| 2022 | $6,058.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $3,020.00 | Wellesley Century |
| 2020 | $2,090.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,163.33 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $5,417.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $4,835.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $4,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $5,155.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $3,373.00 | Wellesley to Bourne (1-Day, Sat) |
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