| Melissa Halstead Halstead | $100.00 |
| Marcie Ellis | $150.00 |
| Carole Harbison | |
| John Tobin | $250.00 |
|
Deborah Linder |
$120.00 |
| 2025 | $670.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $6,000.60 | Sturbridge to Provincetown Inn (2-Day) |
| $1,500.00 | PMC Unpaved | |
| 2023 | $6,061.00 | Sturbridge to Provincetown Inn (2-Day) |
| $1,500.00 | PMC Unpaved | |
| 2022 | $4,131.00 | Reimagined |
| $1,500.00 | PMC Unpaved | |
| 2021 | $3,140.00 | Wellesley Century |
| 2020 | $4,482.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,165.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $4,950.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $5,012.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $4,834.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $4,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $4,300.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $4,325.00 | Sturbridge to Provincetown Inn (2-Day) |
