| 2025 | $0.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2024 | $15,155.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $14,455.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $17,092.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $14,371.00 | Reimagined |
| 2020 | $14,980.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $13,980.20 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $13,677.25 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $15,525.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $20,315.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $35,895.85 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $11,025.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $10,520.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $4,482.50 | Sturbridge to Provincetown Monument (2-Day) |
