Celebrate Highwood is excited to announce the 17^th annual Great Highwood Pumpkin Festival, October 2 - 4, 2026. This family friendly, fan favorite 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 Avenue), along Green Bay Avenue (between Highwood and North Avenues), Everts Park (111 North Avenue), 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 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.

“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 American Place Casino and Culver’s, our donors and everyone who helps us bring it all to life.”

This year, Celebrate Highwood is excited to 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 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 1, 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.