| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| $0.00 | PMC Unpaved | |
| 2024 | $15,529.32 | Sturbridge to Provincetown Inn (2-Day) |
| $4,036.00 | PMC Unpaved | |
| 2023 | $19,617.10 | Sturbridge to Provincetown Inn (2-Day) |
| $4,520.00 | PMC Unpaved | |
| 2022 | $15,606.53 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $19,230.00 | Wellesley Century |
| 2020 | $6,295.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $8,561.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $9,205.67 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $6,880.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $5,915.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $5,762.00 | Sturbridge to Provincetown Inn (2-Day) |
