| Pamela Greene | $50.00 |
| Paige Hopkins | $200.00 |
|
Eliza Fortenbaugh |
$100.00 |
|
Anonymous |
$200.00 |
|
Anne Finucane |
|
|
Amy Baron |
|
|
Heather Erlandson |
|
|
Jason Goldstein |
|
| Betsy Kimmel | $118.00 |
|
Anonymous |
$1,000.00 |
| 2025 | $2,243.00 | Wellesley to Bourne (1-Day, Sat) |
| 2024 | $11,625.20 | Sturbridge to Bourne (1-Day, Sat) |
| 2023 | $16,871.94 | Wellesley to Bourne (1-Day, Sat) |
| 2022 | $11,837.10 | Wellesley to Wellesley (50 mile Sunday) |
| 2021 | $14,630.59 | Wellesley to Wellesley (50 mile Sunday) |
| 2020 | $6,040.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $13,485.88 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $25,360.60 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $17,547.08 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $16,221.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $19,409.81 | Sturbridge to Provincetown Monument (2-Day) |
| 2014 | $12,730.00 | Sturbridge to Provincetown Monument (2-Day) |
