Highwood Pumpkin Fest Returns with Carnival, Live Music, and Fun‑filled Contests

Mark your calendars, because the 17th Great Highwood Pumpkin Festival is rolling into town from October 2 through October 4, with a community‑wide pumpkin‑carving preview on the evening of October 1. It’s the kind of hometown celebration that feels both familiar and fresh, especially after a bustling summer of local events.

The festival isn’t confined to a single spot. Instead, the fun spreads across four key locations: City Hall on 17 Highwood Ave., the stretch of Green Bay Road between Highwood and North avenues, Everts Park at 111 North Ave., and the Metra Station parking lot where the carnival kicks into high gear. Along these streets you’ll find food trucks, drink vendors, artisan stalls, two towering pumpkin walls, and hands‑on carving stations that invite both kids and grown‑ups to try their luck.

Music lovers will gravitate toward the two stages set up for the weekend. The J. Blanton Main Stage anchors the North Avenue‑Green Bay Road area, while the Everts Park Pavilion—sponsored by American Place Casino—hosts its own lineup. Expect a mix of local bands, upbeat covers, and a few surprise guests, all keeping the atmosphere lively from afternoon until the lights go down.

If competition is your thing, you’re in luck. Contests pop up throughout the grounds, from the “Curdtoberfest” pumpkin‑carving showdown in the City Hall lot (thanks to Culver’s) to costume parades for pets and kids, and even a pumpkin‑pie‑eating face‑off on Sunday afternoon. And let’s not forget the quirky Micro NASCAR Racing event, brought to life by Field’s Auto Group.

Behind the festivities lies a heart‑warming purpose: SaLT—Service and Learning Together—will receive all proceeds. This student‑run, volunteer nonprofit tackles food insecurity, offers tutoring, and steps in during community crises. Every ticket, every slice of pie, and every ride helps fuel their mission.

Here’s a quick snapshot of the schedule:

• Thursday, Oct 1: Community pumpkin carving (4 – 9 pm) and unlimited carnival ride specials (5 – 9 pm).
• Friday, Oct 2: Festival opens at 4 pm; trick‑or‑treating (4 – 6 pm); live music (4 – 10 pm); rides and games (5 – 10 pm).
• Saturday, Oct 3: Gates swing open at noon; music runs noon‑10 pm; rides 1 – 10 pm; Great Pumpkin Wall lighting at 7 pm.
• Sunday, Oct 4: Starts at noon; pet costume contest (12 pm), kids’ costume contest (1 pm), pumpkin‑pie‑eating contest (2 pm).

All of this is made possible thanks to generous sponsors like American Place Casino, Culver’s, Field’s Auto Group, and countless local volunteers. As Jessica Ortega, President of Celebrate Highwood, puts it, “The Great Highwood Pumpkin Fest is a perfect way to welcome fall, bring our community together, and give back. We couldn’t do it without the support of our neighbors and partners.”

For the latest updates on performers, vendor lists, and any last‑minute changes, swing by the Celebrate Highwood website or the official Highwood Pumpkin Fest page. Grab your pumpkin‑spiced latte, wear your coziest sweater, and join the town for a weekend that’s equal parts spooky, sweet, and community‑spirit.