| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $6,136.25 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $6,050.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $6,964.72 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $6,025.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $5,784.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $5,886.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $5,584.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2017 | $6,069.65 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $4,569.18 | Sturbridge to Provincetown Inn (2-Day) |
