| Emily Dowling | $150.00 |
| michelle prior | $40.00 |
|
Anonymous |
$500.00 |
| Cynthia Lasker | $500.00 |
|
Gary Blank |
$120.00 |
|
Annette Herz |
$100.00 |
| 2025 | $1,410.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $10,059.80 | Sturbridge to Provincetown Inn (2-Day) |
| $4,500.00 | PMC Unpaved | |
| 2023 | $6,000.00 | Wellesley to Provincetown Inn (2-Day) |
| 2022 | $2,000.00 | Reimagined |
| 2021 | $2,120.00 | Reimagined |
| 2020 | $5,989.44 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $8,525.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $4,975.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $5,100.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $4,700.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $4,500.50 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $4,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $6,700.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $4,300.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2011 | $4,830.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2010 | $4,500.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2009 | $0.00 | PMC |
| 2008 | $5,780.00 | Sturbridge to Provincetown Monument (2-Day) |
