October is flying by, and this is the stretch where the calendar gets wonderfully full: 5K mornings, brewfest Saturdays, the last farmers market Sundays of the season and the final countdown to Halloween. 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.
Saturday, October 10: a 5K morning on both sides of the state line
If you like starting the weekend with a little movement, you have two great options this Saturday. Orland Park's Sosa Trot 5K takes off at Turtlehead Lake, a scenic course through one of the village's best parks, and it is the kind of community race where you will see neighbors, not just runners. Over in Crown Point, the Fall Fest Run for the Hills 5K and 2K starts at the Crossroads YMCA as part of the city's fall festival weekend. Pick your side of the state line, and if you are not racing, come cheer: race mornings are a wonderful way to feel a town's energy.
October 16 and 17: Munster laughs, Valparaiso celebrates
Friday night, October 16, the Cloister in the Woods in Munster hosts a Chicagoland stand-up comedy show at 7:30 p.m., a fun date-night option on the Indiana side. Then Saturday, October 17 is a big one in Valparaiso, with three events in a single day. The Autumn Promenade runs downtown from noon to 4:30 p.m., a ticketed stroll through shops and activities that has become a fall tradition. MAACtoberfest at the Montdale Park complex starts at noon with food and family fun. And Brewski Fest takes over Central Park Plaza at 5 p.m. for the adults in the group. If you have friends considering a move to Valparaiso, this is the weekend to bring them: they will see a downtown that knows how to celebrate.
Friday, October 23: Valparaiso trick-or-treats downtown
Valparaiso's Downtown Trick-or-Treat lands Friday, October 23, when local shops 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 the trunk-or-treats and haunted hayrides already on the calendar that same weekend.
Saturday, October 24: a full day in Crown Point and Orland Park
Crown Point packs October 24 with two very different events. The Crown Point Anime-Fest takes over the Lake County Fairgrounds starting at 10 a.m., with vendors, cosplay and programming for fans of all ages. Later in the afternoon, the SPARTA DOME Autumn and Craft Fair opens at 3 p.m. at 1355 East North Street, a cozy indoor market that is perfect for early holiday shopping. Meanwhile on the Illinois side, the Hello Kitty Cafe Truck parks at Orland Square in Orland Park, a fun stop for the younger set, and Mokena's Halloween Mayhem at Main Park runs noon to 3 p.m. with a trunk or treat, haunted trail and monster market all in one afternoon.
Sunday, October 25: Tinley Park's Boo Bash and the last market Sundays
Tinley Park's Boo Bash lands Sunday, October 25, the park district's family Halloween celebration, and it is a great way to close the weekend. And do not let the season slip away without one more farmers market morning: the Frankfort Country Market holds its final Sundays at Breidert Green through October 25, and the Tinley Park fall market wraps up around the same time. Fresh produce, flowers and handmade goods, one last time this year.
Friday, October 30: Boos and Brews in Portage
Portage sends October out in style with Boos and Brews Brewfest on Friday, October 30, a Halloween-costume brewfest that has become a favorite on the Indiana side. Costumes encouraged, I am told. And for the brave ones, Valparaiso's Sanctum 2026 runs October 30 and 31 for a properly spooky Halloween night.
Halloween weekend is almost here
By the time you read this, the town-by-town Halloween plans are locked in: Frankfort's Safety Trunk or Treat on the morning of October 31, Crown Point's official trick-or-treating from 5 to 7 p.m., and trunk-or-treats across the region. The season belongs to you this weekend: a race morning, a brewfest, a last market Sunday, a costume parade. 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 and 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!™