| 2024 | $17,086.00 | Reimagined and Volunteer |
| 2023 | $12,065.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $18,275.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $15,846.00 | Wellesley Century |
| 2020 | $14,653.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,894.75 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $6,716.00 | Sturbridge to Provincetown Inn (2-Day) |
