Great Highwood Pumpkin Fest 2025: Carving Pumpkins, Live Music, and Fall Magic in Chicagoland

Every October, the North Shore gets loud, lit, and carved up with the Great Highwood Pumpkin Fest. Now in its 15th year, the legendary fall throwdown returns October 3–5, and it’s more than just a festival—it’s a full-blown takeover of downtown Highwood. Streets transform into a swirling autumn carnival of glowing gourds, live music, carnival rides, and every fall-flavored bite you can imagine.

This isn’t just about carving jack-o’-lanterns (though you’ll find plenty of those). It’s about community. Each pumpkin carved—at just a $2 suggested donation—funnels back into SaLT, a local nonprofit lifting up families in need. That means every flickering smile cut into orange flesh carries a deeper purpose.

Expect the chaos of kids racing between rides, the smell of cider doughnuts and pumpkin beer filling the air, and bands cranking live music to keep the vibe rolling into the night. Add in massive fall-themed installations and the festival turns Highwood into one giant, glowing canvas of seasonal magic.

Fifteen years in, Pumpkin Fest isn’t just a tradition—it’s a North Shore institution. It’s where suburban charm collides with rock ‘n’ roll energy, proving that fall in Chicago doesn’t have to mean raking leaves—it can mean dancing in the street with a cider in one hand and a pumpkin carving knife in the other.

So grab your crew, sharpen your carving skills, and head north. Highwood’s Pumpkin Fest is where fall hits full throttle.

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