Stretching over 2,400 miles from Chicago to Santa Monica, Route 66 - dubbed the "Main Street of America" - was established in 1926 as a critical highway connecting the Midwest to the West Coast.

Though officially decommissioned in 1985, its spirit lives on, drawing road-trippers with its promise of freedom, nostalgia, and adventure. Let’s dive into what makes this highway such a legendary trip, and why Route 66 remains a bucket-list road trip for travelers around the globe.

The Starting Point: Chicago, Illinois

Starting your Route 66 journey in Chicago? Make sure to stop by the Route 66 Begin Sign at Adams Street. The city offers many pre-adventure highlights: Millennium Park, the Art Institute, and of course, some of the best deep-dish pizza around. Chicago sets the tone with a mix of city sophistication and classic Americana, preparing you for the vast landscapes ahead. Starting here lets you rev up for the full Route 66 experience, beginning in the bustling cityscape and transitioning to the open road.

Kitsch and Quirkiness in Pontiac, Illinois

Next stop: Pontiac, home to the Route 66 Hall of Fame and Museum. This museum, free to enter, showcases the history and unique charm of the Mother Road, with quirky murals, vintage cars, and memorabilia. Route 66’s appeal isn’t just in its attractions but in the oddities, like Bob Waldmire’s Hippie Van - a mural on wheels. Pontiac is your first taste of the eclectic spots you’ll find along this famous highway. Plus, there are dozens of vibrant murals throughout the town, making it a photographer’s paradise!

Museum Opening Hours: Daily: 9.00 - 17.00.

A Taste of History in Springfield, Missouri

Missouri’s Springfield, known as the “Birthplace of Route 66”, is a stop you can’t miss. Here, you’ll find the Route 66 Car Museum ($15 entry) with over 60 classic and rare cars on display, like the 1981 DeLorean and a 1926 Hudson. Don’t skip Fantastic Caverns, a ride-through cave (around $28 for adults) that keeps things easy and accessible while giving you a glimpse into Missouri’s geological wonders. Springfield is also home to the first drive-thru, Red’s Giant Hamburg - a must-try for some nostalgic dining.

The Mesmerizing Meramec Caverns in Missouri

About an hour from St. Louis, Meramec Caverns is a 4.6-mile-long cave system offering cool tours of impressive underground formations ($25 for adults). Once rumored to be a hideout for outlaws like Jesse James, these caves bring history to life. Even if you’re not into geology, the caverns make for a unique roadside attraction where you can stretch your legs, cool off, and snap some great photos. This spot epitomizes the spontaneous surprises that make Route 66 so charming.

Retro Vibes at the Blue Whale of Catoosa, Oklahoma

Continuing into Oklahoma, the Blue Whale of Catoosa is one of the most iconic Route 66 landmarks. Built in the early 1970s as an anniversary gift, this 80-foot whale sculpture sits by a small pond, inviting travelers to take a break and snap some fun photos. The Blue Whale encapsulates the quirky and playful spirit of Route 66. It’s free to visit, and there are picnic tables if you want to stop for a snack before hitting the road again.

While Route 66 offers a thrilling sense of freedom, a little planning helps ensure you don’t miss the best parts. Be mindful of gas station locations, as they can get sparse along certain stretches, and keep an eye out for limited service in more rural areas. Lastly, remember to pack some car-friendly snacks and a good playlist to keep the spirit of adventure alive. Ready to make some memories? The open road awaits, so buckle up, and let Route 66 lead you to new adventures!