| Scott Haig | |
| James Patterson-Puertolas | $500.00 |
| Megan Kelly | |
| Jack Murrel | |
| Nathaniel Casey | |
| Reid Williamson | |
| Andrew Carey | |
| Alison Mathews | $100.00 |
| frank seyboth | $200.00 |
| Ivan Loukovnikov | |
|
Anonymous |
$100.00 |
| Don Webster | |
|
Anonymous |
|
| Nick Azrack | |
| Jessica Flynn | $100.00 |
| Eric Utay | $120.00 |
| Michelle Patterson | |
| Ross Goldstein | $120.00 |
|
Margot Connolly Johnson |
|
| John Teahan | $120.00 |
| 2025 | $7,040.00 | Bourne to Provincetown Inn (1-Day, Sun) |
| 2024 | $7,235.66 | Bourne to Provincetown Inn (1-Day, Sun) |
| 2023 | $13,293.66 | Bourne to Provincetown Monument (1-Day, Sun) |
| 2022 | $7,097.00 | Wellesley to Provincetown Inn (2-Day) |
| 2021 | $11,521.60 | Wellesley Century |
| 2020 | $6,601.13 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $11,281.57 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $9,122.31 | Sturbridge to Provincetown Inn (2-Day) |
