| Kevin Ball | $200.00 |
| Michael Lavoie | $200.00 |
|
Don Donovan |
$200.00 |
|
Geoff McIntosh |
$150.00 |
|
John Martin |
$250.00 |
| 2025 | $1,000.00 | Wellesley to Wellesley (50 mile Sunday) |
| 2021 | $2,100.00 | Reimagined |
| 2020 | $1,310.00 | Wellesley to Provincetown Monument (2-Day) |
| 2009 | $4,400.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2008 | $4,120.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2007 | $4,302.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2006 | $2,450.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2001 | $987.00 | Sturbridge to Bourne (1-Day, Sat) |
| 2000 | $1,275.00 | Wellesley to Bourne (1-Day, Sat) |
| 1999 | $1,810.00 | Sturbridge to Provincetown Inn (2-Day) |
