Weekend Ideas: Halloween Events, Haunted Hayrides and the Farm Trail Ahead | Joanne Dal Santo REALTORĀ®

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Weekend Ideas: Halloween Events, Haunted Hayrides and the Farm Trail Ahead

Joanne Dal Santo | October 8, 2026

Halloween has officially taken over the calendar, and honestly, I love this part of the season. The haunted hayrides are rolling, the pumpkin farms are in full swing, and every community has found its own way to celebrate the countdown to October 31. I went back through the event pages this week and verified everything below with the organizers and venues themselves, so you can plan with confidence. As always, give each place a quick check before you head out, since dates and hours can shift with the weather.

October 16: Frankfort's Halloween Bash

Frankfort Park District kicks off the spooky stretch with its Halloween Bash on Friday, October 16 from 5:30 to 8 p.m. at the Founders Community Center on Oak Street. It is a ticketed evening for kids, with games, activities and all the candy your little ghosts can handle, and pre-registration is the way to go since spots fill up. It is the warm, neighborly kind of event Frankfort does so well.

Frankfort's Scarecrow Building Contest is part of the same spirit, with voting running October 13 through 29. Wander the entries, pick your favorite and feel the whole town lean into the season together.

October 15 through 17 and 22 through 24: Portage's Woodland Park Haunted Hayrides

Over on the Indiana side, Portage's Woodland Park Haunted Hayrides run Thursday through Saturday on two consecutive weekends, October 15 through 17 and October 22 through 24, starting at 6:30 p.m. It is a classic haunted hayride through the woods, the kind of family-friendly scare that has become a fall tradition in the Region. Pick your weekend and grab a spot early.

October 23: trunk-or-treats on both sides of the state line

Friday, October 23 is a busy night. The Park District of Orland Park holds a free trunk or treat from 5:30 to 7 p.m., with decorated trunks and candy for the little ones. Meanwhile, Pet Supplies Plus in Crown Point runs its own trunk or treat from 5 to 7 p.m. on East Summit Street. And if you are looking for something a little different, Orland Park's These Hallowed Halls immersive Halloween experience and its Pumpkin Carving Date Night are both worth a look for the grown-ups.

October 24: Mokena's Halloween Mayhem

Mokena Park District brings its Halloween Mayhem to Main Park on Saturday, October 24 from noon to 3 p.m., with a trunk or treat, a haunted trail and a monster market all in one afternoon. It is a great single-stop way to get the whole family into the spirit without bouncing between a dozen events.

The farm trail is in full swing

If you want a whole day of it, the region's pumpkin farms are at their peak right now. On the Indiana side, County Line Orchard in Hobart is the closest U-pick orchard to Chicago, with a ten-acre corn maze, U-pick pumpkins, a kids' farm and the Moo Choo train. Harvest Tyme Family Farm in Lowell calls itself Northwest Indiana's ultimate fall destination, with multiple corn mazes, hayrides and pumpkin picking. And Exploration Acres bills itself as the region's largest corn maze, with twenty-two acres and about ten miles of trails. On the Illinois side, Siegel's Cottonwood Farm in Lockport has its fifteen-acre corn maze and Cottonwood Railroad train rides, and Bengtson's Pumpkin Farm in Homer Glen is a long-running favorite. A quick note: this year's spring frost limited the U-pick apple crop, so call ahead to confirm picking status before you plan around apples.

Halloween weekend is right around the corner

Looking ahead to October 31, the town-by-town plans are taking shape. Frankfort's police host a Safety Trunk or Treat from 10 a.m. to noon at the Breidert Green parking lot, kicked off by the E.F. Bucko costume parade at 10 a.m. Crown Point's official trick-or-treating runs 5 to 7 p.m. on Halloween, and Orland Park's village has set its hours for the same day. For the brave ones in the family, Valparaiso's Amhurst Asylum extreme haunted house runs through October, and New Lenox's Curse of Glas House is open through the Halloween season.

Make a weekend of it

This is the stretch of October where the season belongs to you: a hayride under the lights, a trunk or treat with the neighbors, a slow afternoon wandering a corn maze. These are the small traditions that make a place feel like home. And if you are weighing a move to any of these towns, come spend a weekend first: feel the community before you ever tour a house. That is when you know. When you are ready to make the move for real, I would love to be in your corner. You Can With Joanne!™

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