The Great Highwood Pumpkin Festival is a FREE, family-friendly fall celebration featuring three days of pumpkin carving, live music, carnival rides, children’s and pet costume contests, trick-or-treating, pumpkin pie eating contests, food and artisan vendors, seasonal interactive installations, and more!
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 and community carving stations, along with special activations including Culver’s “Curdtoberfest” and Micro NASCAR Racing sponsored by Field’s Auto Group.
The festivities will kick off with a special Community Pumpkin Carving night on Thursday, October 1 from 4–9 PM, along with unlimited carnival ride specials. Then, throughout the weekend, guests can enjoy live music across two stages, carnival rides and games, trick-or-treating, and plenty of fall-themed activities for the whole family.
Sunday will feature some of the festival’s fan-favorite contests, including the Pet Costume Contest, Kids Costume Contest, and Pumpkin Pie Eating Contest at Culver’s “Curdtoberfest.” On Saturday evening, guests can also gather for the Great Pumpkin Wall Lighting at 7 PM.
This year’s festival will once again benefit SaLT (Service and Learning Together), a volunteer-led nonprofit that supports food-insecure families, provides academic tutoring, aids communities in crisis, and inspires compassion and leadership through service-learning.

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