The city of Highwood is ready to make pumpkin-carving history this fall as they also attempt to break the Guinness World Record for the most jack-o’-lanterns lit in one location. Everyone is welcome to include their own carved creations into the winning total. The four-day festival includes pumpkin pie cooking and eating contests, the Pumpkin Fest Parade and a giant pumpkin regatta, featuring pumpkin flotillas on Lake Michigan. The event culminates on Saturday evening with the anticipated lighting of 32,000 jack-o’-lanterns. October 20 to 23; visit CelebrateHighwood.com for more information.