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Coolest Places Along Route 66: Cities, Towns, Restaurants - Business ...
This year marks Route 66's centennial, making it the perfect time to plan an epic road trip. Lauren Durie 2026-04-04T12:09:01.234Z I love the quirk and nostalgia of Route 66, also known as the Mother Road. I was surprised by wild burros, an ancient civilization, and a live streamed steak-eating contest. I'd recommend that all drivers stop in Pontiac, Illinois, and Oatman, Arizona. 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 The Pink Elephant Antique Mall in Livingston, Illinois, offers treats, trinkets, and more. Lauren Durie 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 st...
The Ultimate Route 66 Road Trip Itinerary | roadsrufer
The Most Iconic Stops from Chicago to Santa Monica A Route 66 road trip itinerary is not about following a single continuous road. Much of Route 66 no longer exists in one piece, and trying to trace it exactly often means missing the best stops. The experience comes from the contrast between structured towns, preserved landmarks, and more remote stretches. This Route 66 road trip itinerary shows you where to stop, how long it takes, and how to plan your route without turning it into a checklist. For a deeper breakdown of timing and trade-offs, see this Route 66 road trip planning guide. Traveling by RV gives you the flexibility to adjust your pace. Route Chicago ➝ Pontiac ➝ Tulsa ➝ Amarillo ➝ Tucumcari ➝ Albuquerque ➝ Holbrook ➝ Kingman ➝ Amboy ➝ Santa Monica Distance ~2,400 miles Trip Duration 2–3 weeks Best For First-time Route 66 road trip travelers Best Time April to June / September to October Trip Style Iconic stops + flexible pacing Chicago → Pontiac · 100–110 miles · 1.5–2 hours drive Stop 1: IllinoisWhere does Route 66 start in Illinois? Route 66 starts in downtown Chicago, and it’s the most practical and clearly defined place to begin your road trip. For most Route 66 road trip itineraries, this is the default starting point and the most straightforward place to begin planning your route. As you leave the city, the drive quickly shifts into smaller towns and quieter roads. This is one of the most structured parts of a Route 66 road trip, with stops close together and minimal gaps between them. Early on, driving Route 66 here feels easy to follow, with frequent landmarks that make it simple to get into the rhythm of the trip. Best for First-time Route 66 road trip planners: A clear starting point that makes building an itinerary easier Travelers who prefer frequent stops: Short distances between towns reduce long driving stretches Those interested in Route 66 history: A high concentration of preserved landmarks early in the route Things to do Chicago Route 66 Begin Sign: The official starting point for a Route 66 road trip itinerary Pontiac (Murals & Route 66 Museum): One of the more engaging towns, with multiple stops grouped together Polk-a-Dot Drive-In (Braidwood): A classic diner stop with a more local, less curated feel Standard Oil Gas Station (Odell): Small and easy to visit, better as a quick stop than a detour Recommended stay: Half a day to 1 day is enough to cover the key stops without slowing down your overall Route 66 roa...
A practical guide to driving Route 66 | National Geographic
A practical guide to driving Route 66 It's no wonder the legendary Mother Road remains a road trip firm favourite — but where to begin with such an epic journey? Read on and buckle up.
Bob Dylan Painted 6 Iconic Sites Along Route 66, and I Took a Road Trip ...
To celebrate the centennial of Route 66, writer Matt Kirouac traces Bob Dylan's artwork along the Mother Road.
