The Backyard Tourist

Cultural Road Trips Within One Tank of Gas

“The Scenic Route for the Culturally Curious.”

Route 66-Pontiac, IL

Have you ever rolled down your windows on an unseasonably warm February day? It’s the kind of day that makes you think, this is why I love the open road. Then you already understand the magic of Route 66 in Illinois. It’s a great drive all year long.

That first road trip on a sunny warm-ish day feels extra special. This feeling is especially strong after being housebound. This typically occurs during the coldest, darkest part of the year. It follows the recovery from the busy holiday season. Was that really only 6 weeks ago?

In the Midwest, we call it “Fools Spring.” It occurs approximately 6 weeks after the holidays. It comes immediately before we get a few more strong doses of Midwest Winter. It’s a great day for a drive on Route 66!

Driving along the most storied stretch of U.S. Route 66, Pontiac isn’t just a stop. It’s a place that makes you pull over. You wander longer than planned. There is so much to see! You may seriously consider extending your road trip by a day. And you SHOULD! In my opinion, people simply do not plan enough time to see all of the Route 66 sites in Illinois. They leave Chicago. They don’t have enough time to enjoy Joliet, Wilmington, Pontiac and all of the cool sites along the way. They rush to get to Springfield, or St. Louis. This planning error causes them to miss a lot of really great roadside stops.

I’ve driven the “First Hundred Miles” of Route 66 more times than I can count. Every time, Pontiac feels like a love letter to the Midwest. It is creative, artsy, a little quirky, and endlessly welcoming.

Below are my Backyard Tourist favorite spots to see in Pontiac.

Photo by Kelly Klobucher, February 2026

A Museum Lover’s Surprise

Here’s what surprises first-time visitors: Pontiac isn’t just a one-museum town! Here, museums help drive the local economy.

The Route 66 Hall of Fame & Museum

Let’s start with the obvious must-see: the Route 66 Association of Illinois Hall of Fame and Museum. If you have read this blog for long, you know I always highlight the best museums and historic sites! The museum also has a visitor’s center

This museum is housed in a historic fire station and former City Hall. There are several exhibits and museums throughout the building. You can read more about how this building was saved. I cover how it was turned into museums in my blog about Pontiac Museums here.
This place has EVERYTHING. It is a treasure chest of neon signs, vintage gas pumps, license plates and road maps. You’ll find the kind of memorabilia that makes you nostalgic for a road trip you haven’t even taken yet.

Illinois Rt 66 Museum anchors the town’s Route 66 legacy. Housed in a historic fire station, this museum is overflowing with nostalgia. Its shelves and walls display license plates, vintage signs, maps, and stories from the highway. These items helped define American travel along Route 66. The tales unfold from Chicago to California. They even include relics like the actual VW van of famed Route 66 artist Bob Waldmire.

Passionate Docents and Volunteers are on hand. They are eager to tell stories about the Mother Road’s heyday. They want to ensure you see the best Pontiac has to offer. Trust me, you’ll want to linger.

Upstairs is a wonderful exhibit of Bob Waldmire’s art. An unexpected surprise. Don’t miss it! It is one of the coolest Route 66 Exhibits in Illinois.

Bob Waldmire’s art is on display upstairs. He drove Route 66 and was a prolific artist who documented life and culture along Route 66. He is the inspiration for “Fillmore” in the Pixar movie Cars. This is a must see
The Livingston County War Museum

History buffs will appreciate the powerful exhibits at Livingston County War Museum Upstairs from the Route 66 Museum. It is one of the largest military museums in Illinois. The museum is filled with deeply personal artifacts. These include hundreds of complete uniforms. Men and women of Livingston County wore them while serving our country. These artifacts tell stories far beyond textbooks. If you scan a QR code on many of the uniforms, you can see video clips and oral recordings. The wearers of the uniforms retell their history in these recordings.

Museum of Gilding Arts

Just a block away across from city hall, road trippers will find the Museum Of The Gilding Arts. It is one of my favorite surprises anywhere on Route 66. Here you’ll uncover the shimmering world of gold leaf. You’ll learn how it’s made and its history, which stretches back to ancient times. You’ll also discover how gilding has been used in architecture, signage, and art. The museum offers a hands-on experience. It is fascinating and unlike any other small-town museum I’ve stumbled into. This includes demonstrations and beautiful displays that make this craft come alive.

The Pontiac Oakland Museum
Photo by Kelly Klobucher, December 2019

Further down the block, Car enthusiasts should carve out time for Pontiac Oakland Automobile Museum. Classic Pontiac and vintage Oakland cars gleam under soft museum lights. Whether you’re nuts about auto history or you’re just curious about the brands. These brands helped shape automotive culture. The stories here are as polished as the chrome.

The Museum showcases beautifully restored classic cars that gleam like chrome dreams. Even if you’re not a gearhead, there’s something irresistible about stepping back into the golden age of American driving.

But the magic doesn’t stop inside the museums!

Pontiac’s downtown is an open-air art gallery. It is home to more than two dozen massive murals. They celebrate Route 66 and Pontiac history and Americana. Wandering mural to mural feels like a scavenger hunt for the soul of the Midwest. Bring comfortable shoes — and your camera. This town is infinitely Instagram-able!

For a town of roughly 12,000, the cultural density is really impressive!

Where to Eat (Because the best Road Trips Are Built Around Meals)

Road trips are measured in meals, and Pontiac delivers.

B’s Rally Point is where great vibes meet incredible flavors. The local loyalty tells you you’re in the right place.

For a full Route 66 vibe, grab a bite at Edinger’s Filling Station. The vintage décor and roadside nostalgia make every burger feel like part of the journey.

Wally’s is not just a gas station. It is a destination! The BBQ, prepared foods and walls of snacks make this worth a stop! My last visit here I spent more on snacks and merch than I did on gas! 🙂

Shop Small, Discover Big

Downtown Pontiac is tailor-made for wandering. Locally owned boutiques, antique shops, and specialty stores line streets that feel refreshingly unhurried. You’ll find Route 66 souvenirs, retro signs, handmade gifts, and unexpected treasures.

It’s the kind of place where shop owners chat, ask where you’re from, and genuinely thank you for stopping in.

Why Pontiac Feels Different

Some Route 66 towns lean hard into nostalgia but feel frozen in time. Pontiac feels alive.

There’s pride here in preservation. There’s pride in storytelling. There’s pride in welcoming travelers who are chasing something slower and more meaningful than an interstate exit.

You come to check out a town with the same name as a car.
You stay for the museums and murals.
You leave already planning your next visit.

So the next time you’re cruising U.S. Route 66 and you see the sign for Pontiac, don’t just pass through.

Pull over.
Wander the museums.
Talk to people.
Order the pie.

This stretch of the First Hundred Miles of the Mother Road isn’t just about where you’re going. It’s about discovering a Midwest town. This town knows exactly why you started your journey. They can’t wait for you to visit!