Coolest Places Along Route 66: Cities, Towns, Restaurants

Most people drive Route 66 for the nostalgia — the neon signs, the diners, the echoes of road trips past.

As someone who loves seeking out things you didn’t know you wanted on your travel bucket list, I prefer ridiculous over retro, and let me tell you: The Mother Road was the mother lode of quirk. I found Route 66 to be a tribute to America’s weird, wacky, and wonderful in the best way possible.

From a town with more burros than people to the remains of a prehistoric Native American city, if you’re celebrating Route 66’s 100th anniversary this year, these are some of the unique stops I found worth pulling over for.

There are several must-visit stops in Illinois

Route 66 may start in Chicago, but I think Pontiac, Illinois, is the best place to officially get your bearings.

The Bob Waldmire Experience, located in the same complex as the Route 66 Hall of Fame & Museum, is the best place to learn about the road’s most famous explorer. A nomadic artist, Waldmire used a VW bus and “road yacht” — a converted double-decker school bus — as a studio on wheels, making him one of the OG van lifers.

Snap a photo with the iconic Route 66 Shield Mural before driving about two and a half hours south to Livingston, Illinois, home of the Pink Elephant Antique Mall.

This historic building, once a high school, offers just about everything you could ask for: Alongside the massive maze of trinkets and goods, you can buy sweet treats at the Mother Road Fudge-n-Candy and eat a meal at the retro Twistee Treat Diner.

I donned my best “Grease” getup and took advantage of all the photo ops there, too — including an oversize ice-cream cone, a giant UFO, and a bubblegum-pink elephant.

Keep driving toward Missouri, and you’ll approach Cahokia Mounds, a UNESCO World Heritage Site. I loved exploring the archaeological remains of the largest pre-Columbian city north of Mexico by walking the self-guided earth mound trails, then popping into the Interpretive Center to learn more.

Head to Amarillo, Texas, for steaks the size of your head and oversize art to match

For Texas-sized Route 66 fun, the Big Texan Steak Ranch & Brewery looks more like a small town than a restaurant.

It’s best known for the 72-ounce steak challenge, which began in the 1960s as a competition between cowboys to see who could out-carb each other. Now, the challenge is open to anyone willing to attempt the feat.

Finish the spread in under an hour, and it’s free; fail, and it’s $72. Nearly 100,000 people have tried, with roughly 10,000 succeeding. Oh, and anyone attempting the challenge is live streamed.

I kindly passed — the restaurant serves regular meals, too — but I commend anyone who gives it a shot.

There’s more to explore at Big Texan, too, including live music, a shooting gallery, and covered wagons and cabins for overnight stays.

While you’re in Amarillo, Cadillac Ranch is another must-see. The iconic public art installation features vintage Cadillacs buried in the dirt.

Everyone is encouraged to leave their mark — quite literally, with spray paint — meaning it looks a little bit different every time you go. I found it oddly therapeutic knowing whatever I added wouldn’t be permanent.

Catch a shootout reenactment and befriend wild burros in Oatman, Arizona

The only traffic you’ll usually find on the stretch of Route 66 from Kingman to Oatman is of the four-legged variety. A historic ghost town where wild burros now outnumber people, Oatman actually served as an inspiration for Disney’s “Cars”.

The wild burros descend from pack animals used by miners during the Gold Rush years. Local shops sell bags of food, and if you feed them, they’ll quickly try to become your best friends. (Fair warning: They do nip, and one almost ripped my dress.)

Tourists are encouraged to feed and photograph the burros as long as they don’t have a sticker on their head, which means they’ve been tagged as a baby or as needing a special diet.

Time your visit right, and you could also end up in the middle of a reenacted shootout on Main Street — which I found equally thrilling and unhinged.

For another outlaw experience along Route 66, the Grand Canyon Railway in nearby Williams, Arizona, offers a vintage train ride to the national park with “bandits” as carmates. A road trip, after all, is only as good as the characters you meet along the way.