| Laura Schneider | $1,750.00 |
| Liz and Bob Burke | $250.00 |
| 2025 | $2,000.00 | Reimagined |
| 2020 | $1,060.00 | PMC Rider |
| 2018 | $4,900.00 | Wellesley to Provincetown Inn (2-Day) |
| 2015 | $4,500.00 | Wellesley to Provincetown Inn (2-Day) |
| 2014 | $6,980.00 | Wellesley to Provincetown Inn (2-Day) |
