| 2025 | $0.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $11,523.55 | Wellesley to Provincetown Inn (2-Day) |
| 2023 | $11,280.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $8,065.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $9,100.00 | Wellesley to Provincetown Monument (2-Day) |
| 2020 | $3,355.00 | Wellesley to Provincetown Inn (2-Day) |
| 2019 | $5,415.00 | Wellesley to Bourne (1-Day, Sat) |
| 2018 | $8,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2009 | $3,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2007 | $4,130.00 | Wellesley to Provincetown Inn (2-Day) |
| 2006 | $3,300.00 | Wellesley to Provincetown Inn (2-Day) |
| 2005 | $0.00 | PMC |
| 2004 | $1,750.00 | Wellesley to Bourne (1-Day, Sat) |
