| 2025 | $0.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $4,730.20 | Wellesley to Bourne (1-Day, Sat) |
| 2023 | $10,577.50 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $11,254.48 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $10,252.60 | Wellesley to Bourne (1-Day, Sat) |
| 2020 | $6,765.00 | Wellesley to Bourne (1-Day, Sat) |
| 2019 | $5,598.99 | Wellesley to Provincetown Inn (2-Day) |
| 2018 | $4,170.00 | Wellesley to Bourne (1-Day, Sat) |
| 2017 | $7,815.00 | Wellesley to Provincetown Inn (2-Day) |
| 2016 | $4,720.00 | Wellesley to Bourne (1-Day, Sat) |
| 2015 | $4,580.00 | Wellesley to Bourne (1-Day, Sat) |
| 2014 | $4,225.00 | Wellesley to Bourne (1-Day, Sat) |
| 2013 | $4,830.00 | Wellesley to Provincetown Inn (2-Day) |
| 2012 | $3,700.00 | Wellesley to Bourne (1-Day, Sat) |
| 2011 | $5,295.00 | Wellesley to Bourne (1-Day, Sat) |
| 2010 | $3,965.00 | Wellesley to Bourne (1-Day, Sat) |
| 2009 | $3,155.00 | Wellesley to Bourne (1-Day, Sat) |
| 2008 | $3,015.00 | Wellesley to Bourne (1-Day, Sat) |
| 2007 | $3,115.00 | Wellesley to Bourne (1-Day, Sat) |
| 2006 | $3,685.00 | Wellesley to Bourne (1-Day, Sat) |
| 2005 | $4,950.00 | Wellesley to Bourne (1-Day, Sat) |
| 2004 | $7,080.00 | Wellesley to Bourne (1-Day, Sat) |
| 2003 | $3,325.00 | Wellesley to Bourne (1-Day, Sat) |
| 2002 | $4,895.00 | Wellesley to Provincetown Inn (2-Day) |
| 2001 | $1,845.00 | Wellesley to Provincetown Inn (2-Day) |
| 2000 | $2,058.00 | Wellesley to Provincetown Inn (2-Day) |
| 1999 | $1,305.00 | Wellesley to Bourne (1-Day, Sat) |
| 1998 | $2,885.00 | Wellesley to Bourne (1-Day, Sat) |
| 1997 | $2,555.00 | PMC Rider |
| 1996 | $1,815.00 | PMC Rider |
| 1995 | $1,305.00 | PMC Rider |
| 1994 | $1,075.00 | PMC Rider |
| 1993 | $1,162.50 | PMC Rider |
