| 2025 | $0.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $7,457.66 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $6,912.00 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $10,909.00 | Wellesley to Bourne (1-Day, Sat) |
| 2021 | $6,286.00 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $5,533.00 | Wellesley to Bourne (1-Day, Sat) |
| 2019 | $4,675.00 | Wellesley to Bourne (1-Day, Sat) |
| 2018 | $4,000.00 | Wellesley to Bourne (1-Day, Sat) |
| 2017 | $6,593.00 | Wellesley to Provincetown Inn (2-Day) |
| 2013 | $3,200.00 | Wellesley to Bourne (1-Day, Sat) |
| 2004 | $200.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $2,675.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2002 | $4,640.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2001 | $4,675.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2000 | $3,415.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1999 | $3,410.00 | Sturbridge to Wellesley (2-Day) |
| 1998 | $2,574.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1997 | $2,534.00 | PMC Rider |
| 1996 | $2,000.00 | PMC Rider |
| 1995 | $2,510.00 | PMC Rider |
| 1994 | $2,006.00 | PMC Rider |
| 1993 | $900.00 | PMC Rider |
