Started on Halloween evening in 2015 the annual Winona Woods Jack-O’-Lantern Contest started as an event where residents participated by carving pumpkins and delivering them to the event display. Each pumpkin was then displayed along Chelsea Road from 5-9 PM. Trick for Treaters and other visitors then vote for their favorites. Prizes are given to Best in Show, Best Pumpkin 12 and Under, Friendliest, and Most Horrifying.
After a break from tradition in 2016 the event was revived in 2017 as an online competition where residents took photographs of thier creations and uploaded them to social media with the tag #WinonaWoodsGreatPumpkin. Votes were calculated by the most “reactions” to the entries and a winner was chosen based on that criteria. Moving the contest to an online format doubled participation and allowed residents to keep thier pumpkins to display for trick-or-treaters at thier homes.