Spanning over 2,400 miles across eight states, Route 66 is more than just a road — it’s a slice of American history. Big cities, small towns, roadside diners and desert landscapes, Route 66 has it all. It offers a nostalgic, quirky, and unforgettable journey. Whether you’re driving it from Chicago to Santa Monica or picking a section to explore, here are 10 unmissable places to check out along the way.
1. Route 66 Start Sign – Chicago, Illinois
Your journey officially begins in downtown Chicago at the corner of Adams Street and Michigan Avenue, where the “Begin Route 66” sign marks the start of the legendary route. Before heading west, soak in the buzz of the Windy City — grab a deep-dish pizza, visit the Art Institute of Chicago, or take a stroll along Lake Michigan. It’s the perfect mix of urban energy before the open road.
2. Gateway Arch – St. Louis, Missouri
Nicknamed the “Gateway to the West,” the Gateway Arch is the tallest monument in the U.S., standing at 630 feet. Located right on the banks of the Mississippi River, it’s an essential Route 66 photo stop. Take the tram to the top for sweeping views of St. Louis, then walk through the adjacent Museum of Westward Expansion to get in the pioneer spirit.
3. Meramec Caverns – Stanton, Missouri
Just off Route 66 lies the spectacular Meramec Caverns, a system of underground caves made famous by colourful lighting and a bit of outlaw lore. Legend has it that Jesse James used them as a hideout. The cave tour is both visually stunning and full of fascinating geological formations, from towering stalagmites to dramatic underground waterfalls.
4. Cadillac Ranch – Amarillo, Texas
An unmissable stop for art lovers and road trippers alike, Cadillac Ranch is a bizarre and brilliant roadside installation featuring ten vintage Cadillacs buried nose-first in the ground. Visitors are encouraged to bring spray paint and leave their own artistic touch. It’s messy, weird, and wonderfully Route 66.
5. The Blue Whale – Catoosa, Oklahoma
One of the most beloved roadside attractions on the route, the Blue Whale of Catoosa was built in the 1970s as a gift from a husband to his wife. Today, this giant, smiling whale resting in a pond is a surreal and charming photo op. There’s a picnic area nearby, making it a good spot to take a break and enjoy the nostalgic surroundings.
6. Petrified Forest National Park – Arizona
Part natural wonder, part time machine, the Petrified Forest National Park offers landscapes unlike anywhere else in the US. Ancient trees turned to stone, sweeping desert vistas, and multi-coloured badlands create a truly alien world. Route 66 once ran through the park, and you can still see a vintage car marking the original path.
7. Wigwam Motel – Holbrook, Arizona
Looking for a quirky overnight stop? Check into the Wigwam Motel, where you’ll sleep inside a concrete teepee. Built in the 1950s, it’s a classic example of mid-century Americana. The site also features vintage cars parked outside each “wigwam,” completing the nostalgic vibe.
8. Standin’ on the Corner Park – Winslow, Arizona
Made famous by the Eagles’ song “Take It Easy,” this tiny park in Winslow, Arizona pays homage to the lyric “Standin’ on a corner in Winslow, Arizona…” The mural, statue, and parked flatbed Ford make for a fun and quick stop that perfectly captures Route 66 charm and musical history.
9. Oatman – Arizona
This quirky ghost town-turned-tourist-stop is nestled in Arizona’s Black Mountains. In Oatman, wild burros roam the streets freely — descendants of the donkeys left behind by gold miners. With its Old West storefronts, saloons, and daily staged gunfights, Oatman feels like a movie set come to life.
10. Santa Monica Pier – California
End your journey at the Santa Monica Pier, the official western terminus of Route 66. There, you’ll find the iconic “End of the Trail” sign, an amusement park, restaurants, and beach views that make for a perfect finale. Dip your toes in the Pacific Ocean and reflect on the miles, stories, and memories you’ve collected along the way.
Final Tips for Your Route 66 Road Trip
- Budget plenty of time. Route 66 is not a trip to rush. Allow time to get off the highway and explore the side attractions.
- Mix old and new. Some sections of the original route no longer exist, so mix historic stretches with modern detours using a reliable Route 66 guide or app.
- Expect the unexpected. From giant fibreglass statues to vintage diners, some of the best moments come from the least expected stops.
- Support local. Many Route 66 towns rely on tourism, so shop local, eat at family-run diners, and stay in mom-and-pop motels.
Ready to Hit the Road?
Route 66 isn’t just about getting from point A to B. It’s about the journey, the people you meet, and the stories you collect along the way. Whether you’re a first-timer or retracing its steps, these 10 stops will help make your Route 66 experience one to remember. If you’re visiting from abroad, don’t forget to check if you’re eligible for an ESTA before starting your Route 66 adventure. Check out our USA page for expert advice on getting an ESTA!