| 2024 | $6,329.80 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $6,770.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2020 | $0.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2019 | $5,250.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2018 | $4,985.83 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $4,802.00 | Sturbridge to Provincetown Inn (2-Day) |
