
Thursday, October 1 - Community Night & Opening Carnival
Friday, October 2 - Sunday, October 4. 2026
View Pumpkin Fest website for complete information
Leashed Dogs Are Welcome
The Great Highwood Pumpkin Festival is the biggest outdoor celebration on Chicago’s North Shore featuring all-you-can-carve pumpkins, nightly lightings of pumpkin-filled walls, carnival rides, costume and pumpkin pie eating contests, trick or treating, two stages with live music, seasonal interactive installations, food and beverage vendors and so much more!
Thank you to our 2025 sponsors
Dimeo Brothers
Founders All Day IPA
Goose Island 312 Wheat Ale
Michelob Ultra
Skimmers
Spaten Oktoberfest
Stella Artois