The Great Highwood Pumpkin Festival

10/16/2025

Can’t get enough pumpkins? 🎃
Catch Grow at Wayfarer Theaters, opening tomorrow, October 17! The same crew who presented the pumpkins at The Great Highwood Pumpkin Fest is bringing the fall magic to the big screen. You won’t want to miss it! 🎬✨

10/14/2025

10/10/2025

The 15th Annual Great Highwood Pumpkin Festival wouldn’t have been possible without our amazing sponsors and volunteers who help make this community tradition shine brighter every year. 🎃✨

We’re so grateful for your support—from helping us carve 10,000 pumpkins to keeping the fun going all weekend long! 🙌

Thank you to our sponsors: T-Mobile, Renewal by Andersen of Chicago, Drinkpurebloom, Montessori Kids Universe Bannockburn, Lakeshore Beverage, Kern Heating & Cooling Co., The Home Improvement Network, College of Lake County, American Place Casino, 5-Hour Energy, Elite Remodeling Group, ComEd, Lifeway Kefir, Leafguard Brand Gutters, Demuth Inc., Highwood Redevelopment Associates, Christopher B. Burke Engineering, Ltd., Uline, Ablaze Design Group, Compass, North Shore Gas, Klein, Thorpe & Jenkins, Ltd., Mindy Moore, Bernardi Securities, Dimeo Brothers, and The Dog Stop. 🧡

And, thank you to our incredible volunteers: your energy, enthusiasm, and dedication helped make this weekend truly unforgettable. 💛

📸 Photography by Eric Toalson

10/10/2025

💃✨ Thank you to Step 2 this Dance Studio for their amazing flash mob Saturday night! Your energy and talent brought an extra dose of fun to the festival and had everyone on their feet. What a way to light up Highwood! ✨💃

Check out their full performance here!: https://www.facebook.com/share/v/17oNSvEayD/

📸 Photography by Eric Toalson

10/09/2025

🏎️✨ Thank you to Porsche Exchange for driving our festival forward with their support year after year!

Your continued support fuels the magic of The Great Highwood Pumpkin Festival—and this gorgeous car is proof they know how to make an entrance! ✨🏎️

10/09/2025

🍟✨ We’re still savoring McCain Foods USA’s incredible activation at the festival!

From giving away their famous French fries to making our event the inaugural stop of the Golden Fries for Golden Moments Tour, their support was unforgettable.

We’re honored to have partnered with McCain and can’t wait for more tasty moments in the years to come! ✨🍟

📸 Photography by Eric Toalson

10/08/2025

🏎️✨ Thank you to J. Blanton Plumbing for powering the Pumpkin Speedway and making the race a highlight of the festival!

From the lined-up cars to the scoreboard, they helped bring speed and excitement to everyone in attendance.

Your support keeps the wheels turning and the fun rolling—literally! We can’t wait to see them in action next year! ✨🏎️

📸 Photography by Eric Toalson

10/08/2025

🎃✨ Thank you to Wayfarer Theaters for presenting the pumpkins that made this year’s Great Highwood Pumpkin Festival a huge success!

🎥 Continue the celebration and don’t miss their upcoming movie Grow, about a little girl with a talent for growing giant pumpkins, opening October 17 at Wayfarer Theaters!

We’re so grateful for their continued support in bringing fall magic to Highwood! 🎃✨

10/06/2025

Congratulations to our Pet Costume Contest Winners! Thank you to The Dog Stop for sponsoring the prizes and making this contest paws-itively amazing! 🎉🐾

🥇 First Place: Heather Remack & Poppy (Cocker Spaniel) – Tick-Tock Croc
🥈 Second Place: Kim Conroy & Oreo (Poodle Mix) – Magpie Kpop Demon
🥉 Third Place: Sylvia Kopek & Roxy (Chihuahua) – Flying Monkey

We’re totally wagging our tails over these adorable costumes! Which one stole your heart?! 🐶✨

📸 Photography by Eric Toalson

10/04/2025

Highwood Pumpkin Fest Contests are TOMORROW! 🎃📣

Here’s your Sunday lineup at School of Rock Highwood on Highwood Avenue:

🐾 Pet Costume Contest — 12:00 PM
✨ Kids Costume Contest — 1:00 PM
🥧 Pumpkin Pie Eating Contest, proudly sponsored by J. Blanton Plumbing — 2:00 PM

It’s still not too late to sign up!
Register at https://www.highwoodpumpkinfest.com → Select “Schedule” → “Events”
A $5 donation/entry fee helps support SALT: Service and Learning Together.

Come in costume, bring your furry friends, and don't forget your appetite. See you there! 🧡

10/03/2025

Join Bluey and Cinderella at Pumpkin Fest at the haywagon on Highwood Ave. from 3-4 pm TOMORROW!

Meet Cinderella at her “pumpkin carriage” and get some great photos with both characters, courtesy of DeMuth.