Greendale trustees set 2026 trick-or-treat for Oct. 31 after heated debate over Gift of Wings weekend

The Village of Greendale Board of Trustees voted to hold the 2026 community trick-or-treat on Saturday, Oct. 31, from 4 to 7 p.m., and asked village organizations to assist Gift of Wings so the nonprofit could preserve as much of its multi-day Halloween programming as possible.

The decision followed more than an hour of public comment and trustee discussion at the February meeting, where residents and several trustees offered sharply different views about tradition, logistics and the effect on a longstanding community event known as Gift of Wings. The Public Celebrations Committee had recommended shifting trick-or-treat to Sunday, Oct. 25, to avoid conflicting with Gift of Wings Saturday programming, but the board ultimately approved the Saturday date with a motion that included a request for additional village support.

Why it mattered: Gift of Wings runs an annual multi-day Hallowe'en program that includes pumpkin carving, music, a parade and a costume contest. Event organizer Scott Fisher told trustees the activities rely on multiple days of volunteer manpower and that ‘‘we can—————’t do all of that stuff on Saturday’’ without losing key elements such as pumpkin-throwing, parade timing and the costume contest. Residents urged both sides: some said the actual holiday should be preserved; others prioritized keeping Gift of Wings intact.

Board debate focused on several trade-offs. Supporters of moving trick-or-treat to Oct. 31 argued that many residents had asked for the holiday date and that surrounding communities often hold trick-or-treat on Saturdays. Opponents warned that forcing Gift of Wings to compress its weekend could impose unsustainable staffing and financial burdens on a largely volunteer-run event that, Fisher said, ‘‘costs us over $12,000 to put on’’ and often runs at a loss.

Trustees also discussed possible mitigation: starting the parade earlier on Sunday, enlisting other local groups to help with setup, or adopting an ordinance that would automatically set trick-or-treat timing for similar calendar conflicts in future years. Several trustees cautioned against using an open online survey to resolve the question, noting such polls can be gamed.

The final motion approved by the board included a request that other Greendale organizations and the village provide assistance to Gift of Wings to help preserve as much of the event as possible. The roll-call vote recorded Ayes from Trustees Barbee, Unger, McFaul and Ollette; Trustees Beckmeyer and President Zabrowski voted No. Scott Fisher said there was still a ‘‘possibility that we may not be able to do it’’ exactly as in prior years but affirmed he wanted to continue the event.

Next steps: The board did not change the parade or costume contest rules at this meeting; staff and trustees said they would coordinate with Gift of Wings and community groups to identify areas where the village could provide manpower or promotion ahead of the October event.