Celebrate Highwood presents the American Place Casino Great Highwood Pumpkin Festival Oct. 2-4

Celebrate Highwood has announced the 17th annual American Place Casino Great Highwood Pumpkin Festival, running Oct. 2-4, 2026. This family friendly event will offer three days of pumpkin carving, live music from two stages, children’s and pet costume contests, pumpkin pie eating contests, trick-or-treating, seasonal interactive installations, a variety of food and artisan vendors, full bars, a carnival and more.

The Great Highwood Pumpkin Fest grounds will be spread throughout Highwood at Highwood City Hall, 17 Highwood Ave.; along Green Bay Road between Highwood and North Avenues; Everts Park, 111 North Ave.; and in the Highwood Metra Station parking lot, where a full carnival will be located. Streets will welcome food, drink and activity vendors as well as two large pumpkin walls and carving stations (in front of City Hall and along North Avenue), with special activations including Culver’s “Curdtoberfest,” Micro NASCAR Racing sponsored by Field’s Auto Group and more.

Attendees will enjoy three days of live music and contests from two stages throughout the fest grounds, including the J. Blanton Main Stage at North Avenue and Green Bay and the Everts Park Pavilion sponsored by American Place Casino, with contests taking place at Culver’s “Curdtoberfest” at Highwood City Hall parking lot.

Festival hours are 4-10 p.m. Friday, noon to 10 p.m. Saturday and noon to 9 p.m. Sunday. Carnival hours are 5-9 p.m. Thursday, 5-10 p.m. Friday, 1-10 p.m. Saturday and 1-9 p.m. Sunday.

“The Great Highwood Pumpkin Fest has become such a special part of what makes Highwood Highwood, and it’s the perfect way to welcome fall after a very busy summer of events,” says Jessica Ortega, president of Celebrate Highwood and owner of Giggles Play. “At the heart of it, this festival has always been about bringing people together, celebrating our community and doing some good along the way. None of it happens without the people and organizations who show up for Highwood, and we’re incredibly grateful to our sponsors, including our naming rights partner, American Place Casino. We also are grateful to Culver’s for bringing their ‘Curdtoberfest’ activation and all of our other amazing sponsors and everyone who helps us bring it all to life. It’s our sponsors that allow us to continue bringing these large-scale events to our beloved community, for all to enjoy free of charge!”

This year, Celebrate Highwood will once again support SaLT (Service and Learning Together) as their beneficiary. With a focus on celebrating the power of community and local impact, Celebrate Highwood values SaLT as a volunteer nonprofit, led by passionate students and veteran educators, that supports food-insecure families, provides academic tutoring, aids communities in crisis, and partners with local groups, while inspiring compassion and leadership through service-learning.

In keeping with tradition, this year’s festivities will begin with a special community prelude to Pumpkin Fest night from 4-9 p.m. on Thursday, Oct. 1, with pumpkin carving and a full carnival with rides, games and food. Highwood restaurants, businesses, and bars will be open for business as well.

For a full music lineup and schedule, visit celebratehighwood.org or HighwoodPumpkinFest.com. The weekend activities and events schedule will be constantly updated as activities are confirmed.