Event Details
Celebrate Highwood will host its 17th annual Great Highwood Pumpkin Festival throughout downtown Highwood on Oct. 2-4, 2026. The free, family-friendly festival will feature pumpkin carving, live music, carnival rides and games, trick-or-treating, children’s and pet costume contests, pumpkin pie eating contests, food and artisan vendors, seasonal installations and more.
The festival will begin with Community Pumpkin Carving on Oct. 1 from 4-9 p.m., followed by a full weekend of fall festivities. Highlights include the Great Pumpkin Wall Lighting at 7 p.m. Saturday, along with the Pet Costume Contest, Kids Costume Contest and Pumpkin Pie Eating Contest on Sunday.
Festival activities will take place throughout Highwood, including Highwood City Hall, Green Bay Avenue, Everts Park and the Highwood Metra Station Parking Lot, which will host a full carnival. Attendees can also enjoy two large pumpkin walls, community carving stations, Culver’s “Curdtoberfest” and Micro NASCAR Racing sponsored by Field’s Auto Group.
The 2026 festival will benefit SaLT (Service and Learning Together), a nonprofit supporting food-insecure families, academic tutoring, communities in crisis and service-learning initiatives.
Come celebrate the season, enjoy some fall fun and experience one of Highwood’s favorite annual traditions!