The 10 Best Major Cities on Route 66 You Need to See

USA - Illinois - Chicago - Downtown Chicago & Lake Michigan
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Dreaming of a Route 66 road trip and not sure where to stop along the way? While the best parts of the Mother Road are often exploring the off-beat places and hidden gems, you also want to take advantage of spending some time in the best major cities on Route 66.

Whether you have enough time to spend a few days in each, or you only have a few hours, here are the best large cities on Route 66 that you should consider adding to your itinerary.

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Major Cities on Route 66

The Best Major Cities on Route 66

I’m listing these from east to west, since that’s the most “traditional” way to drive the route (the west to east is just as valid).

Chicago, Illinois

USA - Illinois - Chicago - Classic Architecture in Chicago

Since the purpose of Route 66 was to connect Chicago to Los Angeles, it would be strange if we didn’t start with Chicago as our first important city to visit on Route 66. You can even start your road trip at the official Route 66 starting point!

If you have two or three days to explore Chicago before taking off, make sure to visit the Chicago Art Institute, drive Lake Shore Drive, and eat a true deep dish pizza. You can also take in a baseball game or basketball game, depending on the time of year you choose to visit.

I love arts and culture travel, so I suggest you check out the works of Frank Lloyd Wright in Chicago and the surrounding area!

St. Louis, Missouri

USA - Missouri - St. louis downtown at twilight in USA

Did you know that the St. Louis Arch is actually a National Park? Of course, there’s so much more to do in St. Louis than just ride to the top of the arch (though that’s a great place to start).

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You can take a river boat cruise on the mighty Mississippi River, take a free tour of the Budweiser factory, and check out the city’s fabulous art museums!

Tulsa, Oklahoma

USA - Oklahoma - Tulsa - Tulsa, Oklahoma, USA downtown skyline on the Arkansas River in the afternoon.

Tulsa is home to some great Oklahoma hidden gems like the mystical Center of the Universe. It also has some famous Route 66 signage and great eats.

Tulsa is a culture lovers paradise. While here, check out the world-class Philbrook Museum, the Gilcrease, and aHHa Tulsa. You can also stay for a performance of the Tulsa opera.

Oklahoma City, Oklahoma

USA - Oklahoma - Oklahoma City - Skyline of Oklahoma City, OK with OKC sign and ferris wheel

Many believe that Oklahoma has the best stretch of Route 66 as far as hidden spots to check out, but Oklahoma City is also a great stop on Route 66. As you approach, you’ll see the gorgeous Arcadia Round Barn in the city’s suburbs, along with Pops service station and the Rock of Ages Farm.

If you can spend two full days in OKC you can ride the ferris wheel, visit the Oklahoma City Bombing Memorial, the fabulous Oklahoma City Museum of Art, and enjoy a night out in Bricktown.

As an OKC native, let me suggest you dedicate more than one meal to our local Tex-Mex scene. Chellinos and Ted’s are both excellent options, but there are great new finds opening up all the time!

Amarillo, Texas

USA - Texas - Amarillo - Historic City Hall of Amarillo, Texas, USA

This city in the Texas panhandle might get overlooked compared to other Texas cities like San Antonio and Dallas, but it’s worth spending a little time in Amarillo on your route!

Check out the Cadillac Ranch, an ultra-kitschy sculpture made from real cars. You’ll also want to check out the floating mesa and the Second Amendment Cowboy.

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Essentially, Amarillo is a kitsch-lover’s paradise with big city amenities. So it’s basically perfect.

Santa Fe, New Mexico

USA - New Mexico - New Mexico Museum of Art, Santa Fe, New Mexico USA

So technically Santa Fe is no longer on Route 66, but it was on the original Route. You can take what’s called the Santa Fe Loop up to see it. It will not take you far off the path of the current route, and I think it’s more than worth it!

While here, check out the Georgia O’Keefe Museum along with important historic sites from when New Mexico was a part of Mexico (Old Mexico?) like the San Miguel Chapel.

Albequrque, New Mexico

USA - New Mexico - Albuquerque - Balloons over the Rio Grance

You may not know much about Albuquerque now, but I promise you that you should spend at least two days here if you can manage! This is a truly gorgeous city, and one that is overlooked far too often!

The Sandia Peak Tramway gets you high above the city to some spectacular views. You’ll also want to spend time at the Petroglyphs National Monument.

Between these two sites you’ve already spent a whole day in the city before you’ve gotten to do any traditional Route 66 activities or enjoy any of the city’s cultural sites. See why you should try to spend at least two days here!

Flagstaff, Arizona

USA - Arizona - Flagstaff - Cityscape view of Birch Avenue and San Francisco street signs with clock tower in Flagstaff, Arizona.

This city has an adorable historic downtown to explore and tons of Route 66 sites right within its city limits.

It’s also the home of the Lowell Observatory. If you can spend a night in Flagstaff then you’ll be able to tour the observatory at night for one of their indoor astronomy shows.

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Though it’s not the most popular place to visit the Grand Canyon from on Route 66, if you want to use it as a base to explore the greater area you can do a Grand Canyon day trip from here.

Los Angelos, California

California - Los Angeles - Young woman at the top of Hollywood, Los Angeles, California

Hollywood Boulevard? The Hollywood sign? Griffith Observatory? There’s obviously enough things to do in LA to spend a few days here, but if you only have one I suggest you stick to one area and try to avoid actually driving in LA. Traffic will eat up all of your sightseeing time.

Santa Monica, California

USA - California - Santa Monica beach lifeguard tower in California USA

Santa Monica pier is the perfect place to end your Route 66 road trip. Santa Monica is a separate city from Los Angeles, so don’t confuse your time in these two cities!

Make sure you get a photo with the official Santa Monica: End of Trail sign!

There really isn’t a better way to relax at the end of your long road trip than dipping into the water, walking around with sand between your toes, and riding the famous ferris wheel on Santa Monica Pier!

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Major Cities on Route 66

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