
Pumpkins, Music & Fall Fun at Highwood Pumpkin Fest!
Saturday, October 3, 2026 · 3:00 PM CDT · Highwood Library & Community Center · Highwood, IL
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About this event
Join us for one of the North Shore’s most popular fall festivals! 🎃🎶🍂 The Great Highwood Pumpkin Festival features enormous pumpkin displays, food and artisan vendors, carnival rides, live music, seasonal activities, and full bars. The afternoon is family-friendly, so children are welcome. We’ll enjoy food, music, and fall fun, then stay for the **Great Pumpkin Wall lighting at 7:00 p.m.** 🎃✨ **Saturday, October 3** **3:00–9:00 p.m.** **Downtown Highwood** **📍 MEETING LOCATION** We will meet outside the **Highwood Library & Community Center**, 102 Highwood Avenue, between **3:00 and 3:20 p.m.** At 3:30 p.m., we’ll walk into the festival together. I’ll be wearing a nametag. You can also text me at **312-375-7815** when you arrive. **🎶 LIVE MUSIC** There are two stages, with these bands playing during our visit and into the evening: **J. Blanton Main Stage** * **2:30–4:30 p.m. — Reality Bites:** ’90s rock covers. * **5:00–7:00 p.m. — Roger That:** Surf music, British Invasion, and rockabilly. * **7:30–10:00 p.m. — Davidson County:** Modern and classic country favorites. **American Place Casino Everts Park Pavilion** * **2:30–4:30 p.m. — Acoustic Jukebox:** Acoustic rock, pop, and country favorites. * **6:00–9:00 p.m. — Navy Band Great Lakes “Horizon” Rock Band:** Top 40, classic rock, Motown, and funk. **🪑 BRING A CHAIR** Feel free to bring a folding chair if you’d like to sit and enjoy the bands! Set it up in an appropriate spot in the music area. Bring a warm layer for the evening. **🎟️ ADMISSION** Admission is free. Food, drinks, carnival rides, and other purchases are at your own expense. Leashed dogs are welcome. **🚗 PARKING & TRAIN** Festival parking will be limited, and several downtown streets and lots will be occupied by the event. Allow extra time to find legal street or public-lot parking outside the festival grounds. The easiest option may be taking the **Union Pacific North Metra line to Highwood station**, directly beside the festival. The…