Celebrate Highwood is excited to announce its 15th annual Great Highwood Pumpkin Festival, October 3-5, 2025. This family friendly, fan favorite event will offer, three days of live music from three stages, children’s and pet costume contest sponsored by The Dog Stop, pumpkin pie eating contests, trick or treating, seasonal interactive installations, a variety of food and artisan vendors, full bars, a carnival, and more! And, to kick it all off, the iconic Pumpkin Fest skeletons will be going up throughout Highwood beginning the weekend of September 27 to get the community in the Fall spirit, with the Skelebrity Walk of Fame, sponsored by Porsche Exchange.

The Great Highwood Pumpkin Fest grounds will be spread throughout Highwood at Highwood City Hall (17 Highwood Avenue), Everts Park (111 North Avenue), and the Highwood Metra Station Parking Lot, where a full carnival will be located. Street closures of Green Bay Road from North Avenue to Highwood Avenue, and Highwood Avenue from Green Bay Road to Waukegan Avenue, 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 pumpkins presented by Wayfarer Theaters, featuring the movie Grow.

Attendees will enjoy three days of live music and contests from three stages throughout Fest grounds, including the J. Blanton Main Stage at North Avenue and Green Bay, the Everts Park Pavilion, and the Highwood Redevelopment Associates Stage on Highwood Avenue, where the contests will take place.

Don’t miss The Great Highwood Pumpkin Speedway, 2-9 PM, Saturday & Sunday, where you can take the micro NASCAR style racing wheel at the J. Blanton Plumbing Car Racing Track, with cars sponsored by J. Blanton Plumbing, Wayfarer Theaters, Demuth, Christopher Burke Engineering, and Bernardi Securities.

In celebration of the 15th annual Great Highwood Pumpkin Fest, fall-themed interactive installations will be set up throughout Downtown Highwood. These displays will be available all month long, encouraging visitors to explore the area, snap festive photos, support local businesses, and soak in all that Highwood has to offer.

“The Great Highwood Pumpkin Fest put Highwood on the map, and it’s the perfect kick-off to Fall after our summer series of events,” says Jessica Ortega, President of Celebrate Highwood and owner of Giggles Play. “This year is all about celebrating community and helping raise funds for Pumpkin Fest and our beneficiary.”

This year, Celebrate Highwood is excited to announce SaLT (Service and Learning Together) as the beneficiary of The Great Highwood Pumpkin Festival 2025. 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 support food-insecure families, provide academic tutoring, aid communities in crisis, and partner 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 on Thursday, October 2, from 4–9 PM, with a full carnival with rides, games and food, and pumpkin carving. Highwood restaurants, businesses, and bars will be open for business as well.