| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $10,145.65 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $6,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $20,179.80 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $12,393.84 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $2,500.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $7,950.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $7,220.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $7,915.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $5,075.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $5,000.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $5,673.68 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $5,625.00 | Sturbridge to Provincetown Inn (2-Day) |
