| 2024 | $6,000.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $7,607.60 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $3,056.00 | Wellesley Century |
| 2020 | $1,035.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $5,910.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $5,200.00 | Sturbridge to Provincetown Monument (2-Day) |
