| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $18,881.56 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $26,505.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $27,930.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $34,540.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2020 | $44,098.31 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $22,955.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $17,925.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $20,107.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $13,050.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $11,654.25 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $12,680.62 | Sturbridge to Provincetown Monument (2-Day) |
