The Great Highwood Pumpkin Fest
Fri, Oct 03 – Sun, Oct 05, 2025
17 Highwood Avenue, Highwood, IL 60040
The Great Highwood Pumpkin Festival and Skeletons on Display returns in 2025 as the biggest outdoor celebration on Chicago's North Shore.
Featuring all-you-can-carve pumpkins, nightly lightings of pumpkin-filled walls, carnival rides, costume contests (for kids and pets), a pumpkin pie eating contest, trick-or-treating, two stages with live music and entertainment, hundreds of skeleton displays, food and beverage vendors, and so much more!
