Great Highwood Pumpkin Festival 2024 in Chicago

Come to the start of the Halloween season, the Great Highwood Pumpkin Festival returns to a North Shore suburb of Chicago with plenty of pumpkins to carve, eat, and illuminate! The festive weekend in Highwood is usually scheduled for early October.

Festival Entertainment

This annual free family event, which has become a tradition for many of its fans, features pumpkin stations, three days of live music on two stages, kids' costume contests, pet costume contests, and pumpkin pie-eating contests. Visitors will have the opportunity to enjoy a variety of food and visit artisan vendors, bars, a carnival, and, of course, attend the Lighting the Pumpkins event.

Great Highwood Pumpkin Festival Highlight

A special kick-off event at the Highwood Pumpkin Fest is Skeletons on Display, held in partnership with the Art Center Highland Park. The exhibition actually spans beyond the festival weekend throughout October and features plenty of life-sized skeletons set up in the streets and businesses across Highwood.

This Skeleton Invasion tradition was birthed in the Covid times, when the festival itself was on hiatus. The first edition featured 300 skeletons! Since then, the display has become a part of the Highwood Pumpkin Fest and has kept getting bigger and better. Note that the show is marked with a different theme each year, and some of its fun-added elements are typically auctioned off at the end of the month.