| 2025 | $0.00 | PMC |
| 2024 | $9,402.75 | PMC Virtual Rider and Volunteer |
| 2023 | $10,150.75 | PMC Virtual Rider and Volunteer |
| 2022 | $9,112.75 | PMC Virtual Rider and Volunteer |
| 2021 | $9,700.00 | Reimagined and Volunteer |
| 2020 | $9,000.00 | PMC Virtual Rider and Volunteer |
| 2019 | $7,005.00 | PMC Virtual Rider and Volunteer |
| 2018 | $8,075.00 | PMC Virtual Rider and Volunteer |
| 2017 | $7,955.00 | PMC Virtual Rider and Volunteer |
| 2016 | $6,610.00 | PMC Virtual Rider and Volunteer |
| 2015 | $5,515.00 | PMC Virtual Rider and Volunteer |
| 2014 | $4,900.00 | PMC Virtual Rider and Volunteer |
| 2013 | $5,305.00 | PMC Virtual Rider and Volunteer |
| 2012 | $4,030.00 | PMC Virtual Rider and Volunteer |
| 2008 | $4,360.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $4,165.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $3,995.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2005 | $3,425.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2004 | $5,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2003 | $4,600.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2002 | $4,025.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2001 | $3,625.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2000 | $4,054.50 | Sturbridge to Provincetown Inn (2-Day) |
| 1999 | $3,075.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1998 | $3,123.00 | Sturbridge to Provincetown Inn (2-Day) |
| 1997 | $3,675.00 | PMC Rider |
| 1996 | $3,057.00 | PMC Rider |
| 1995 | $3,458.00 | PMC Rider |
| 1994 | $3,780.00 | PMC Rider |
| 1993 | $3,020.24 | PMC Rider |
| 1992 | $3,133.00 | PMC Rider |
| 1991 | $3,137.00 | PMC Rider |
| 1990 | $3,191.73 | PMC Rider |
| 1989 | $1,812.00 | PMC Rider |
