October is at its peak, and this is the stretch of the season I love most: pumpkin farm Saturdays, the last farmers market mornings of the year, and a calendar that turns the final two weekends of October into a costume parade across the region. I went back through the village calendars and event pages this week and verified everything below, 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.
This weekend, October 16 through 18: history, harvest and the last market Saturdays
Orland Park's History Hikes return Friday, October 16 and Saturday, October 17, a pair of walks that let you see the village through its past. Check the village's special events page for meeting times and routes, and bring comfortable shoes. It is the kind of event that makes you appreciate how a town grew, block by block.
On the Indiana side, Valparaiso's Autumn Promenade runs Saturday, October 17 from noon to 4:30 p.m. downtown, a ticketed fall stroll with treats from the shops and restaurants along the way. Check in at the Valparaiso Events tent on the courthouse lawn from 11 a.m., then wander the square at your own pace. It is a lovely way to spend a Saturday, and a wonderful introduction to Valparaiso if you are considering a move.
And do not let the market season slip away: the Tinley Park Farmers Market runs Saturdays from 8 a.m. to 12:30 p.m. at Harmony Square through October, so October 17 is one of your last chances for fall produce, flowers and handmade goods. The Frankfort Country Market keeps its Sunday mornings going at Breidert Green through October 25, which means you still have a couple of relaxed market mornings left on the Illinois side.
Pumpkin farm season is in full swing
This is the weekend the pumpkin farms shine. On the Illinois side, Bengtson's Pumpkin Farm and Fall Fest in Homer Glen, minutes from Orland Park and Tinley Park, is open daily through November 8 with its corn maze, pumpkin chucker, carnival rides, petting zoo and haunted barn. Konow's Corn Maze in Homer Glen runs two corn mazes plus hayrides, train rides and a jumping pillow. Siegel's Cottonwood Farm in Lockport keeps its corn maze and pumpkin patch open through November 1. Closer to home, Odyssey Fun Farm in Tinley Park and DeLair's Cornstalk Farm in Orland Park round out the local options.
Across the state line, Johnson's Farm Produce in Hobart holds its Pumpkin Festival weekends through October 31, with u-pick pumpkins and a corn maze. Apple Blossom Trails in Crown Point offers u-pick apples and pumpkins, a corn maze, wagon rides and a farm market. Hidden Creek Farm in Crown Point runs a pumpkin patch and farm market, and Kregel's Pumpkin Patch in Lowell is another favorite on the Indiana side. Whether you pick your pumpkin or just take the hayride, these farms are where fall memories get made.
Friday, October 23: Valparaiso trick-or-treats downtown
Valparaiso's Downtown Trick-or-Treat lands Friday, October 23 from 4 to 6 p.m., when more than a hundred downtown businesses hand out candy and the square fills with costumed kids. It is a gentle, well-lit way to ease into Halloween weekend, and it pairs perfectly with everything already on the calendar that Saturday.
Saturday, October 24: Pumpkin Walk, Halloween Mayhem and a market at the mall
Crown Point's Pumpkin Walk takes over the historic square Saturday, October 24 from 11 a.m. to 1 p.m., a trick-or-treat stroll around the courthouse that has become a town tradition. In Mokena, Halloween Mayhem runs noon to 3 p.m. at Main Park on La Porte Road, with a trunk or treat, a haunted trail and a monster market all in one afternoon. The New Lenox Chamber's Halloween Fest also lands Saturday, October 24; check the chamber's events calendar for times and location. And if you like an indoor option, the NW Indiana Spooktacular Craft and Vendor Market sets up at Southlake Mall in Merrillville on Saturday, October 24 starting at 10 a.m., a good spot for early holiday shopping with the family.
Friday, October 30: a spooky send-off
Portage sends October out in style with Boos and Brews Brewfest on Friday, October 30 at 6 p.m., a Halloween-costume brewfest that has become a favorite on the Indiana side. That same evening, the Witches in the Woods 5K and 2K plus the Hocus Pocus Market take over the Lake County Fairgrounds in Crown Point starting at 6 p.m., a run-walk and market combo for the brave and the crafty. Valparaiso follows with an adult Downtown Trick-or-Treat on Friday, October 30, so the grown-ups get a turn at the candy, too.
Halloween night, Saturday, October 31: the town-by-town hours
The village calendars are locked in, so here is the cheat sheet. Frankfort trick-or-treats from 3 to 7 p.m., and the Frankfort Police Safety Trunk or Treat runs 10 a.m. to noon at the Breidert Green parking lot, opening with the E.F. Bucko costume parade at 10 a.m. Orland Park goes 2 to 8 p.m., Tinley Park 2 to 6 p.m., Mokena 1 to 5 p.m. and New Lenox 3 to 7 p.m. On the Indiana side, Crown Point's official trick-or-treating runs 5 to 7 p.m. For the towns not listed, check your village or city website, since Indiana communities announce their hours in early October.
Make the most of the season
You do not need a big festival to feel October arrive. A History Hike, a pumpkin farm afternoon, a last market Saturday, a costume parade on Halloween morning: these small traditions are what make a place feel like home. And if you are weighing a move, this is a wonderful time to come visit and test the fit. Wander the farms, walk the square, watch the trick-or-treaters go by. That is when you know. When you are ready, I would love to be in your corner. You Can With Joanne!™