Highwood Pumpkin Fest:

For the past seven years, Highwood has held an annual pumpkin fest in hopes of defeating the Guinness World Record for most jack-o’-lanterns carved and lit on display (30,581). The festival typically takes place in early October, spanning over a period of three days, and has gotten lots of recognition from television networks, including HGTV. “Property Brothers,” a well-recognized television show, visited the festival and featured an episode on it in 2013. The abundance of activities are spread among the three days and a carnival, Superhero run/walk 5K, HGTV meet and greet, costume contests, and last but not least, the lighting of the pumpkins along with live music!

Apple Holler:

Sturtevant, Wisc., is home to Apple Holler, which consists of 70-plus acres of land, 30,000 dwarf apple trees, and more than 30 different varieties of apples (the farm also has pears, peaches, pumpkins, and sugar snap peas). Prime time for apple picking is between August until early November, then pumpkin season is all throughout autumn. According to Apple Holler’s website, they claim that their main mission is for the community and visitors around to have a memorable experience with the activities, along with making their homestyle meals with fresh-picked apples.

Richardson Farm:

Richardson Farm has been operating since 1840 and has some of the best fall attractions in the Midwest. The farm is comprised of numerous activities, including a 700′ zip line and 50′ observation tower, “orbiting” (also known as zorbing, the activity involves a certified operator strapping you into an 11′ ball and sending you down a hill), pig races, and, above it all, their world-famous corn maze. With a whopping 33 acres of land, the corn maze is stretched out into five separate maze games, some taking 10-15 minutes to complete, while others can span upwards of two hours! This year, celebrating Star Trek’s 50th anniversary, the farm dedicated the maze’s theme to iconic images from the well-known franchise.

Bagpipes and Bonfire:

Middlefork Farm Nature Preserve in Lake Forest is hosting the celebration of the 29th annual Bagpipes and Bonfires this year. The celebration is based on Scottish heritage, but anyone is welcome to attend the events (for a donation of $100 per adult and $35 per child to help support conservation efforts). The festivities include sheep herding, highland dancers and a picnic feast. Around evening time, the festival concludes with the landing of kilted skydivers, a bagpipes procession and the lighting of the gigantic bonfire made from the brush of buckthorn hedges collected by local volunteers from schools in Lake Forest.

Dungeon of Doom:

Located north of Six Flags in Zion is the Dungeon of Doom. The 42,000-square foot house has more than 15 different varieties of amusement, such as Buried Dead or Alive, Mercy General Asylum Delirium, and Clown Crazy 8’s. The attraction also offers the opportunity to become one of the actors if you have the proper qualifications and experience. The season goes from early September to the first week of November, and prices vary from $25 per visit to $69 for the whole season, if you are a season-pass holder.