Roaming Route 66 Road Trip

There’s never been a better time to hit the open road than in 2026—the year Route 66 celebrates its 100th birthday. Over three epic weeks, you’ll roll from Chicago’s city buzz all the way to the palm-fringed glamour of Los Angeles, tracing the original highway that shaped the great American road trip. Along the way, we’ll detour through quirky roadside diners, retro motels, neon-lit small towns, desert landscapes, and iconic stops that have barely changed since the ’30s. It’s nostalgia, Americana, and pure freedom all rolled into one unforgettable drive.

This centennial year means special events, restored landmarks, and a little extra sparkle along the route—perfect for travellers wanting to experience Route 66 at its most vibrant. From standing on the corner in Winslow, Arizona to watching the sun set over the Grand Canyon, this is the slow-sippin’, wide-grinnin’ adventure you’ll talk about for years.

Illinois kicks things off with Chicago’s legendary skyline, deep-dish pizza, and the official “Begin Route 66” sign that sets the tone for the adventure ahead. Small towns like Pontiac and Joliet bring the nostalgia with murals, museums, and classic diners that feel frozen in time.

Cruise through St. Louis for blues, barbecue, and that iconic Gateway Arch towering over the Mississippi. Missouri’s stretch is loaded with old-school Americana—from neon-lit motels to Meramec Caverns, a favourite hideout of legendary outlaw Jesse James.

Kansas only has 21 km of Route 66, but it packs a punch with the adorable town of Galena and its restored service stations. It’s a quick but charming peek into heartland history, complete with friendly locals and photogenic roadside stops.

Oklahoma offers some of the most authentic, untouched sections of the Mother Road, winding through rolling plains and classic small towns. You’ll find quirky museums, giant roadside sculptures, and a rich Native American heritage woven through the drive.

The Texas Panhandle brings wide-open skies, epic sunsets, and the quirky Cadillac Ranch—where travellers tag spray-painted cars half-buried in the desert. Expect bold flavours, cowboy culture, and long, cinematic stretches of open road.

New Mexico blends desert landscapes with adobe architecture, neon motels, and the heady mix of Spanish and Indigenous culture. Santa Fe and Albuquerque shine with art, markets, and some of the best chilli-infused food on the entire route.

Arizona is Route 66 royalty—home to Winslow, Seligman, and the Grand Canyon, all delivering big Americana vibes and unforgettable scenery. Rugged desert, towering red rock, and historic trading posts make this one of the most memorable legs of the trip.

California welcomes you with orange groves, mountain passes, and the slow shift into that classic West Coast sunshine. The journey ends in Los Angeles at the Santa Monica Pier—where you can celebrate completing Route 66 right at the edge of the Pacific.