| John and Suzanne Bourdeaux |
| 2025 | $500.00 | Wellesley to Provincetown Inn (2-Day) |
| 2024 | $10,880.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2023 | $10,024.15 | Sturbridge to Provincetown Inn (2-Day) |
| 2022 | $17,595.05 | Sturbridge to Provincetown Inn (2-Day) |
| 2021 | $6,385.64 | Reimagined |
| 2020 | $3,295.78 | Sturbridge to Provincetown Inn (2-Day) |
| 2019 | $10,702.53 | Sturbridge to Provincetown Inn (2-Day) |
| 2018 | $11,244.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2017 | $12,684.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2016 | $10,266.75 | Sturbridge to Provincetown Inn (2-Day) |
| 2015 | $10,020.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2014 | $6,910.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2013 | $10,051.00 | Sturbridge to Provincetown Inn (2-Day) |
| 2012 | $9,092.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2011 | $15,605.00 | Sturbridge to Provincetown Monument (2-Day) |
