Highwood’s Great Pumpkin Fest Returns for a Weekend of Autumn Fun

Mark your calendars, neighbors – the 17th Great Highwood Pumpkin Festival is back, kicking off on the evening of Thursday, Oct. 1 and rolling through Sunday, Oct. 4. It’s the kind of hometown fall celebration that feels like a warm hug after a bustling summer.

The festivities are spread out across town, so you’ll be wandering from the festive atmosphere at Highwood City Hall (17 Highwood Ave.) to the bustling Green Bay Road corridor between Highwood and North avenues, then on over to Everts Park at 111 North Ave., and finally to the Metra station parking lot where the carnival lives.

There’s a lot to see and do. Think pumpkin‑carving stations and two massive pumpkin walls that light up the night, food and drink vendors lining the streets, and even a quirky “Curdtoberfest” pop‑up hosted by Culver’s. Car enthusiasts will appreciate the Micro NASCAR Racing track sponsored by Field’s Auto Group – tiny cars, big thrills.

Music lovers, you’re in luck. Two stages will host live performances all weekend: the J. Blanton Main Stage on North Avenue/Green Bay Road and the Everts Park Pavilion, kindly sponsored by American Place Casino. The line‑up changes daily, so there’s always something fresh to catch.

Costume contests? Absolutely. On Sunday you can watch pets strut their stuff at noon, kids show off their creativity at 1 p.m., and the ever‑popular pumpkin‑pie‑eating showdown kicks off at 2 p.m. (If you think you can beat the champion, bring a fork and a lot of appetite.)

Don’t forget the carnival rides – they’re open with unlimited ride specials from 5 p.m. to 9 p.m. on Thursday, then run from 5 p.m. to 10 p.m. on Friday, Saturday, and Sunday. Whether you’re a thrill‑seeker or just in it for the cotton candy, there’s a ride for you.

All of this good‑will is tied to a cause. SaLT – Service and Learning Together – will once again receive the festival’s proceeds. This student‑led nonprofit supports food‑insecure families, offers tutoring, and helps communities in crisis. So while you’re munching on caramel apples, you’re also helping a neighbor in need.

Jessica Ortega, President of Celebrate Highwood and owner of Giggles Play, says the festival “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.” She adds that the community’s generosity – from sponsors like American Place Casino and Culver’s to volunteers on the ground – is what keeps the magic alive.

Want the nitty‑gritty schedule? Thursday night (Oct. 1) starts with community pumpkin carving from 4 p.m. to 9 p.m., followed by unlimited carnival ride specials at 5 p.m. Friday opens at 4 p.m. with trick‑or‑treating, live music until 10 p.m., and rides until 10 p.m. Saturday runs from noon to 10 p.m., highlighted by the Great Pumpkin Wall Lighting at 7 p.m. Sunday’s noon opening features the pet and kids costume contests, then the pumpkin‑pie eating contest at 2 p.m.

For the latest updates, head to the Celebrate Highwood or Highwood Pumpkin Fest websites. Bring your family, bring your friends, and most of all, bring that autumn spirit you’ve been saving for a good reason.