Great Highwood Pumpkin Fest offers pumpkin carving, pumpkin walls, Skeletons on Display and more

Celebrate Highwood is holding its 15th annual Great Highwood Pumpkin Festival Friday through Sunday, Oct. 3-5. This family friendly event will offer three days of live music from three 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. To kick it all off, the iconic Pumpkin Fest skeletons are on display throughout Highwood to get the community in the fall spirit.

The Great Highwood Pumpkin Fest grounds will be spread throughout Highwood at Highwood City Hall, 17 Highwood Ave.; Everts Park, 111 North Ave.; 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.

Attendees will enjoy three days of live music and contests from three stages throughout Fest grounds, including the Main Stage at North Avenue and Green Bay, the Bandshell in Everts Park, and the School of Rock Stage at Highwood and Waukegan Avenues, where the contests will take place.

Main Stage headliners include The Mosquitos, a jam band playing Santana, Stones, Clapton and more at 8 p.m. Friday; Cheap Foreign Cars, a tribute to Cheap Trick, Foreigner and The Cars at 8 p.m. Saturday; and The 9 Nine and 2000s Band, a concept band that specializes in music from the 90s and 2000s, at 6 p.m. Sunday.

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,” said 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 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.

The Great Highwood Pumpkin Fest runs from 4-10 p.m. Friday, noon to 10 p.m. Saturday and noon to 9 p.m. Sunday, Oct. 3-5.

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. 2, with a full carnival with rides, games and food, and pumpkin carving. 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.