Highwood, Illinois, is a tiny town with a giant identity crisis every October. For most of the year, it’s a quiet, historic suburb north of Chicago known for great Italian food and a local vibe. But then the skeletons come out. Well, mostly the pumpkins. If you were looking for the Highwood Pumpkin Fest 2024, you probably expected a few hayrides and some cider. What actually went down was a chaotic, beautiful, orange-tinted takeover of the entire downtown area that drew tens of thousands of people.
It’s loud. It’s crowded.
Honestly, if you don't like the smell of toasted pumpkin seeds and the sound of live cover bands, you'd hate it. But for everyone else, it’s the peak of the fall season in the Midwest. People often confuse Highwood with other local festivals, thinking it’s just another "autumn craft fair" where you buy overpriced knitted mittens. It isn't. Highwood is about the "Walls of Jack-o’-Lanterns." It’s about trying to break world records. It’s about a community that decides to turn its streets into a glow-in-the-dark labyrinth for three days straight.
The Highwood Pumpkin Fest 2024 Reality Check
The first thing you have to understand is the layout. This isn't contained in a park. The festival, officially known as the The Great Highwood Pumpkin Festival, sprawls across the business district, centered around Everts Park and the Metra station. In 2024, the organizers really leaned into the "Celebrating Skeleton" theme alongside the traditional pumpkin towers. It felt a bit like a Tim Burton movie had a baby with a local county fair.
Why do people care so much?
Because of the Guinness World Record attempts. Highwood has a long-standing, friendly (but actually pretty fierce) rivalry with Keene, New Hampshire. Both towns have spent years trying to claim the title for the most lit jack-o’-lanterns in one place. While the 2024 event focused heavily on community spirit and charity—specifically supporting the Make-A-Wish Foundation—that competitive edge still lingers in the air. You can see it in the way the volunteers meticulously stack the orange gourds on those massive wooden scaffolding towers.
Every year, there’s a misconception that you just show up and look at pumpkins. No. You are expected to participate. There are carving stations everywhere. If you didn't leave with orange guts under your fingernails, you basically weren't there.
What Actually Happened at the 2024 Event
The schedule was packed, but not in that corporate, "everything starts exactly on the dot" kind of way. It’s a bit more organic.
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On Friday night, the ceremonial lighting of the towers happened. Imagine thousands of hand-carved faces, ranging from "professional artist" to "toddler with a blunt spoon," all glowing at once. It’s actually pretty moving. The 2024 festival saw a massive turnout for the Pumpkin Pie Eating Contest, which, frankly, is a lot messier than it sounds on the brochure. Watching grown adults face-plant into whipped cream for a trophy is a specific kind of Midwest entertainment you can't find just anywhere.
Music-wise, the 2024 lineup stayed true to the festival's roots. You had local favorites like The Buckinghams or various 80s tribute bands rocking out on the main stage. The sound carries throughout the town, echoing off the brick buildings. It gives the whole place a high-energy hum that doesn't quit until late at night.
The Make-A-Wish Connection
It’s easy to get cynical about festivals, but Highwood puts its money where its mouth is. A huge portion of the proceeds from the 2024 event went to Make-A-Wish Illinois. This isn't just a side note; it's the core of why the festival exists in its current form.
Over the years, the event has raised hundreds of thousands of dollars. When you pay for your parking or buy that overpriced (but delicious) pumpkin ale, you’re actually funding dreams for kids with critical illnesses. In 2024, the "Wish Walls" were a prominent feature, where attendees could read about the specific kids being helped. It adds a layer of emotional weight to the party.
Logistics Most People Forget (Until They’re Stuck)
If you’re planning to hit the next one based on what happened in 2024, listen up. Most people make the mistake of driving into the heart of Highwood at 5:00 PM on a Saturday.
Don't do that.
Parking in Highwood during Pumpkin Fest is a nightmare. It’s a town of 5,000 people trying to host 50,000. In 2024, the smart move—as always—was taking the Metra Union Pacific North Line. The train drops you off literally in the middle of the festival. You step off the platform and you’re immediately staring at a wall of pumpkins. No searching for a $30 parking spot. No walking three miles from a side street.
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- The Skeleton Invasion: The 2024 theme "Skeletons Alive!" meant there were life-sized, themed skeleton displays throughout the town. These were sponsored by local businesses like Bent Fork Bakery or Highwood Small Animal Hospital.
- Pet Parade: Saturday morning featured the pet costume parade. Honestly, seeing a Golden Retriever dressed as a giant taco is worth the price of admission alone.
- The Food: It’s not just pumpkin-flavored stuff. Highwood is a culinary hub. You have local staples like Buffo’s serving up pizzas and burgers alongside festival vendors selling roasted corn and funnel cakes.
The All-Night Carving Marathons
One of the most authentic parts of the Highwood Pumpkin Fest 2024 that doesn't get enough press is the "pre-game." Days before the gates officially open, the town is a hive of activity. Schools, local businesses, and groups of friends gather to carve thousands of pumpkins.
The organizers provide the pumpkins. You provide the labor.
It’s a massive logistical feat. Think about the sheer volume of biological waste. Tons of pumpkin "innards" have to be hauled away and composted. Then, once the festival is over, the pumpkins themselves have to be disposed of. In 2024, the festival continued its commitment to sustainability by working with local farms to ensure the pumpkins were used for animal feed or composted rather than just rotting in a landfill.
Why 2024 Felt Different
There was a different energy in 2024. Maybe it was the weather—it was one of those crisp, perfect Illinois Octobers where the air is sharp but the sun is warm. Or maybe it was just that people were craving that specific brand of communal weirdness that only a "pumpkin world record attempt" can provide.
We saw a shift toward more experiential elements. Instead of just looking at things, there were more interactive "Instagrammable" spots—though the locals would hate me for calling them that. There were giant frames made of gourds and hidden skeleton displays in the alleyways that felt more like an urban scavenger hunt than a traditional fair.
Common Misconceptions Debunked
"It’s just for kids." Not even close. While the day is full of families, Highwood at night is a different beast. The beer garden (The Beverage Garden) is huge. The bands are loud. It’s a massive social scene for adults from all over the North Shore and Chicago.
"Every pumpkin is real." Actually, yes. People often ask if the pumpkins on the high towers are plastic. They aren't. They are real, heavy, organic gourds. This is why the structure of the towers is such a big deal—they have to hold thousands of pounds of weight.
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"It’s free." Well, sort of. While you can walk through parts of the town, the main festival grounds usually require a small per-day donation or entry fee, which goes to charity. It's usually around $5, which is a steal for the amount of entertainment provided.
How to Handle Future Fests Like a Pro
If you missed 2024, you’re probably looking toward the next one. The "Highwood model" is pretty consistent, but you need a strategy to avoid the "I’m overwhelmed and my feet hurt" phase of the evening.
First, go early on Friday. That’s when the pumpkins are the freshest and the crowds are the thinnest. If you wait until Saturday night, you will be shoulder-to-shoulder with strangers. It’s vibrant, but it’s intense.
Second, check the "Pumpkin Count" updates. The festival usually has a running tally of how many pumpkins have been lit. It’s fun to watch the number climb as the weekend progresses.
Third, explore the side streets. Highwood’s downtown is compact, but the festival spills over. Some of the best skeleton displays and smaller food vendors are tucked away off the main drag of Sheridan Road.
Actionable Takeaways for Your Visit
To get the most out of the Highwood experience, keep these specific points in mind:
- Download the Metra Schedule: Don't even try to drive. Use the UP-N line.
- Bring Cash: Many of the smaller vendors and the pumpkin carving stations prefer cash for donations or small purchases.
- Dress in Layers: This is Northern Illinois in October. It can be 65 degrees at 3:00 PM and 40 degrees by 7:00 PM.
- Carve a Pumpkin: Don't just watch. Go to the carving station, pick a pumpkin, and add your own "art" to the wall. It’s the only way to feel like you’re actually part of the event.
- Eat Local: While festival food is fun, try to hit one of Highwood’s actual restaurants. Places like Slyce or Miramar offer a great break from the outdoor chaos.
The Highwood Pumpkin Fest 2024 wasn't just a festival; it was a testament to what a small town can do when it decides to be the best at something incredibly specific. It’s messy, it’s glowing, and it’s arguably the most "Illinois" thing you can experience in the fall. If you want to see the walls of fire and pumpkin guts for yourself, start planning your transit route now, because the crowds aren't getting any smaller.