🎉 The Naperville FunTimes

Your Weekly Family Fun Guide

Issue #33  •  Friday, October 23, 2026

Happy Friday, Naperville families! 🎃

This is the big one. Halloween itself lands next Saturday, but the actual family weekend is this one — pumpkins racing downhill on wheels, trick-or-treating at Naper Settlement’s 1830s houses, and a car wash on 75th that has turned its tunnel into a drive-through haunted house. Downtown parking will be a mess by 11 AM Saturday, so plan accordingly. Jessica DeVries’ fall guide is back down below for everything we couldn’t fit.

📅 This Week’s Top 3 Family Picks

The Naperville Pumpkin Race — Gourds on Wheels, Racing Downhill, Free to Watch 🎃

Someone looked at a pumpkin ten years ago and thought “wheels,” and now it’s a Naperville institution. Decorated pumpkins mounted on axles get released down Rotary Hill two at a time while a crowd yells at them. There’s also a pumpkin decorating contest, a costume contest, games and food vendors, and the whole thing benefits the Turning Pointe Autism Foundation. The 10th annual run is this Saturday. You can just show up and watch for nothing — most people do.

Family Spooktacular — Trick-or-Treating at 1830s Houses, Plus a Disney Tribute Band 👻

Brand new this year, and the premise is good: kids trick-or-treat at the Settlement’s historic homes — the same buildings half of Naperville toured on a third-grade field trip. Add a fright-free haunted house inflatable, slime-making at Ghoul School, canvas painting with Pinot’s Palette, laser tag and food trucks. The headliner is The Little Mermen & The Princess Pals doing two 60-minute Disney sets each day — 10:30 AM and 12:30 PM Saturday, 12:30 and 2:30 PM Sunday. Grown-ups get a Spooky Spirits Bar, which feels fair.

The Haunted Car Wash — Yes, Really. Fog, Scares, and You Never Leave the Car 🚗

A Naperville car wash has turned its tunnel into a haunted house you drive through. Fog, colored lights, live actors and whatever is waiting on the other side of the brushes — and your car comes out clean, which is the part that makes it genuinely funny. It’s eight bucks a car, so a van of four kids costs eight bucks. This is the veteran-owned place on 75th, not the Ace Lane location, and the haunted tunnel runs tonight. Posted hours come from the shop’s own social; double-check their page before you drive over.

👻 Bonus: Your Halloween Cheat Sheet

Back by Popular Demand: Jessica DeVries’ Fall + Halloween Guide

We shared this last week and a lot of you opened it, so here it is again — this is the weekend it earns its keep. Local realtor Jessica DeVries of Southwestern Real Estate keeps a free spreadsheet of fall and Halloween events across the western suburbs: a day-by-day calendar, separate tabs for free and paid, and a color code for little-kid friendly, spooky and scary. Three picks is never going to cover the biggest Halloween weekend of the year. This does. Times and prices move around, so check each event’s own page before you go — she says the same.

Compiled by Jessica DeVries, REALTOR®, Southwestern Real Estate • Instagram @keysfromdevries • Know an event she missed? [email protected]

🍽️ Kids Eat Free This Week!

Both of this week’s deals run on Thursday, Oct 29 — two nights before Halloween, when nobody has the energy to cook anyway.

Two more free ones for Sunday if you still have fuel: Downtown Naperville Trick-or-Treat runs 10 AM to noon, and Halloween Happening at the Riverwalk Grand Pavilion follows from 1 to 4 PM for kids 10 and under. That’s a full Sunday without spending a dollar. Then next Saturday is the real thing, and you’ll have had three dress rehearsals.

Save us a Reese’s,

The Naperville FunTimes Team 🧡