Just 58 days until Halloween!
2nd Annual Sweepstakes
September 2, 2025 through September 30, 2025
Our 2nd Annual sweepstakes runs September 2, 2025 through September 30, 2025.
$250 to one randomly selected winner.
Winner will be selected randomly and announced on October 31, 2025
39th Annual Contest
October 1, 2025 through October 29, 2025
Our 39th Annual contest starts October 1, 2025 and this year we are looking for the true spirit of Halloween. For the chance to win up to $5,000, submit a photo of your family or friends enjoying yourselves while carving and decorating your jack-o'-lanterns. Capture that magical moment, submit the photo, and one of several prizes can be yours.
Submit a picture of your pumpkin and magical family moment through October 29, 2025.
Enter via Pumpkin Masters Woobox submission page.
$5000 Grand Prize Winner
$250 Runner Up Winner
Prize Pack Fan Favorite Winners (4 total)
Prize Pack Fan Favorite Runner Up Winners (4 total)
Winners will be selected by a judge panel of Pumpkin Masters® employees and announced on October 31, 2025. Weekly Fan Favorite Winners will be determined by the entry with the highest number of votes during the Voting Period from October 1 – October 29, 2025.