One of Illinois’s Quirkiest Towns Is Still Flying Under the Radar

A waft of sizzling fries hits my nostrils as I inch down the car window for a snap of the black and white Route 66 sign whirring by. I’m in a quirky town in Illinois, looking for, well, the quirky stuff. It’s the official opening weekend of Route 66’s 100th birthday celebrations, and I’m on the trail of the first 100 miles, from Chicago to Bloomington. Today I’m in Wilmington for the diner menus and odd roadside attractions, but also for the nature side quests that you might forget to look for. 

Where Is Wilmington and Why Is It So Unique

Wilmington is a sleepy, scenic canal town along Illinois Route 66. It’s a bit too far from Chicago to be considered a suburb, and it’s more like a suburb of the Joliet suburb, if that makes sense—an hour from downtown Chicago, and 15 miles south of Joliet. Wilmington has its own distinct vibe of odd and unique. While researching what to do here on Illinois Route 66, I came up with a kaleidoscope of weird and wonderful attractions, from a 20-foot-tall green alien sculpture to bunkers hidden in a tall-grass prairie. Plus, charming, cartoon hamburger murals slapped across the building of a modern burger joint merged with a local brewer. There’s also a quaint shop where you can still get pressed souvenir pennies and then pose with the Route 66 sign. But Wilmington is more than a soft pause along Route 66; it deserves a good half-day of your time.

The Attractions That Define This Quirky Town in Illinois

Because of his metallic green paint job, I thought the Gemini Giant would be an alien. But to me, this super-sized public art installation looks more like a giant Ken doll playing dress up as Buzz Lightyear (from Pixar’s Toy Story). I guess that’s just my millennial interpretation, considering the sculpture was actually built in 1965, during the Space Age. The kids from that era say the Gemini Giant is more representative of Captain Scarlet and the Mysterons, a sci-fi TV series from that decade. Either way, he’s an icon of Route 66, and you can find him in an urban park with a Route 66 sign, mural, and a shop called The Landing Pad.

The shop is tiny and easy to miss, but it has tons of Route 66 memorabilia and souvenirs, including t-shirts, bumper stickers, postcards, posters, and mugs. But my favorite thing in there is another ode to the 1960s (and earlier): a pressed penny souvenir machine. With your own penny and two quarters, you can hand-crank your very own Routee 66 penny. Squeezed between the Gemini Giant and the Landing Pad is a pretty awesome Route 66 mural, even if it does wrap around a bathroom stall. I had to angle myself just right to avoid getting the blue porta-potties in the shot, but somehow, that just added to the quirky charm of it all. 

What It’s Like To Visit Wilmington on Illinois Route 66

Beyond its nostalgic Illinois Route 66 appeal and small-town vibes, Wilmington also has an iconic foodie stop and a decent dose of outdoor adventure. I’m traveling with teens, and that means sandwiches literally have to be sandwiched between the big adventures. We started with a bike ride at Midewin National Tallgrass Prairie. I wanted to go because I adore bison, and I was hoping to see a few calves among their herd of 70. But when we got to the visitor’s center, the ranger laid eyes on the boys and successfully distracted them with a bike trail to the ammunition bunkers. I still don’t know how bison and bunkers go together, but here we are. Within the Midewin National Tallgrass Prairie is the Joliet Army Ammunition Plant, built in the early 1900s to store ammunition and TNT. Today, there are 300 remaining, and it turns out, if you butter up the ranger, he’ll probably tell you how to get one that’s unlocked for the day. It was one of the most unique experiences we’ve ever had in Illinois, and my tween and teen talked about it for days. 

Midewin National Tallgrass Prairie is just 3 miles north of Wilmington, so after our unexpectedly weird bike ride, we grabbed a seat at Nelly’s. It’s a classic reinvention of the Route 66 roadside diner, plopped inside a brew house. The walls are covered in memorabilia, the tables sit between a bar and fermentation tanks, and you order your burgers at the back of the building, creating a walk-up-window dining experience. After plowing through hefty burgers, we hopped back in the car for another Route 66 sidequest, to Kankakee River State Park, about 10 miles southeast of Wilmington. The appeal of this park lies in its canyons, creek, and waterfall, which delivered a big wow factor after a very rainy spring. 

Why It’s Still Flying Under the Radar

Wilmington, Illinois, is one of the small towns that slip under the radar, despite its location along Route 66. Although it’s part of the historic route, most road travelers might take other, faster routes from Chicago to St. Louis, which bypass Wilmington. And beyond notable birthdays and niche celebrations of the historic route, one of the best small towns in Illinois simply doesn’t get much press coverage. There also isn’t much tourist infrastructure: there are no hotels in Wilmington, only a few locally owned restaurants, and no big-box stores. But if you are the kind of road tripper I am, that's precisely why you’d want to go to Wilmington.

Wilmington is the kind of town you might forget about when the world isn’t celebrating Route 66. But if you slow down for a day and dig into the nostalgic vibes and abundant nature escapes, you just might make the memories that make it unforgettable. Whether you think of Buzz Lightyear and bomb bunkers, or pressed pennies and bison, is entirely up to you.