Every October, the small town of Highwood, IL, (about 45 minutes north of Chicago) has a jack-o-lantern competition in attempts to beat the Guinness Book of World Records record for the most lit in one location. The event is fun for all ages. Most of the local restaurants have mini food stands, and the restaurants are all hidden gems! You will also stumble across arts and crafts vendors, boutique popcorn makers, and just about anything that your kids can convince you to purchase spur of the moment.
The event is also very well-organized and people are super friendly. But as it is a small town, parking in Highwood is limited, so take the train from Chicago if you are in for the weekend. And don't miss the big lighting of the pumpkins!