| 2023 | $7,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $6,775.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $4,495.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2020 | $1,450.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $5,335.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $4,925.00 | Sturbridge to Provincetown Monument (2-Day) |
| $500.00 | PMC Winter Cycle |
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