The Ultimate Route 66 Road Trip Itinerary

Route 66 is a historic highway that makes for an ultimate road trip. Also known as the Mother Road or the Main Street of America, it was established in 1926 and, for more than six decades, saw throngs of travelers going westward.

Extending from Illinois to California and passing through several states, it is now a pilgrimage that offers glimpses into the glory days of highway travel. From abandoned towns and dilapidated motels to restored service stations and quirky art installations, the over 2,200-mile journey is far from boring or disappointing.

Are you ready for a unique road trip adventure? Route 66 is waiting for you!

Though you can go from west to east or east to west, for the purpose of this post, I’m exploring the journey westward. Both trips have the potential to be amazing, for me, I’m partial to ending my journey sun-soaking at the beach.

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Illinois

  • Jackson Blvd. at Michigan Avenue/Jackson Blvd. at Lake Shore Drive

Because you are traveling from east to west, you start your Route 66 road trip in Chicago. But where exactly in Chicago? You have two choices: Jackson Blvd. at Michigan Avenue or Jackson Blvd. at Lake Shore Drive. Why are there two? Over the years, the official starting point of Route 66 has changed a few times. If you can’t pick one, why not just visit both? They are only a couple of blocks from each other, so you can easily do this on foot.

  • Joliet Route 66 Welcome Center

Considered by many as an unofficial starting point of Route 66, Joliet is a town that offers a ton of information on Route 66. If you drop by the Route 66 Welcome Center, you can avail of Route 66 exhibits free-of-charge.

  • Route 66 Hall of Fame Museum

For more Route 66 history, a visit to the Route 66 Hall of Fame Museum in Pontiac is a must. With several thousands of memorabilia and artifacts from the prime days of Route 66, it is a fantastic place to learn some great stories about the Mother Road.

  • Gemini Giant

A 30-foot tall statue of man wearing something like a space/welding helmet with a silver rocket ship in his hands, the Gemini Giant is Route 66 landmark located in Wilmington. As it is massive and standing on the side of the road, it will be hard to miss it.

  • Lauterbach Giant

How about a giant muffler man welcoming you as you drive into a service station parking lot? In Springfield, the state capital, you can also find one of these gigantic statues. Called the Lauterbach Giant, it is made of fiberglass and holding a US flag.

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Missouri

  • Park Central Square

Did you know that Springfield, Missouri is the official birthplace of Route 66? If you go to Park Central Square, you will find a plaque that explicitly states this fact. Around the area, you can find other Route 66 attractions, such as the Route 66 Information Visitor Center, Woodruff Building, and Gillioz Theatre.

  • Route 66 Mural Park

An homage to an important time in American history, the Route 66 Mural Park showcases two large murals — The American Ribbon and Cruisin’ into Joplin. Road trippers usually pose for photos with the mural and the classic cars under it so make sure you do the same.

  • Chain of Rocks Bridge

Want to stretch your legs for a bit? Go for a leisurely walk across the Chain of Rocks Bridge. A Route 66 icon, it extends about a mile over the Mississippi River and has a 30-degree turn at the halfway point. It used to be open to vehicular traffic but is now only open to bikers and pedestrians.

  • Gateway Arch

Upon entering St. Louis, you will be greeted by one of the most symbolic American monuments, the Gateway Arch. Constructed in the early 1960s, it is the tallest arch in the world at 630 feet. It is the main feature of the Gateway Arch National Park where you can go relax and picnic while taking in scenic views of the Arch and the blue skies.

  • Mule Trading Post

The city of Rolla may be small but it has its share of Route 66 spots. Sandwiched between the cities of Springfield and St. Louis, it is home to the Mule Trading Post, which is a souvenir stop for road trippers and tourists. Watch out for the large hillbilly sign waving its arms right out front!

  • 66 Drive-in

Fancy having a movie break on your Route 66 road trip? First opened in 1949, the 66 Drive-In is a drive-in theater in Carthage. For just a few bucks, you can watch old or recent Hollywood blockbusters on a 66-foot high and 66-foot wide screen with your fellow travelers inside or in front of your own vehicles.

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Kansas

  • Cars on the Route

The Kansas stretch of the Old US Highway 66 may be the shortest but it holds remarkable history. In Galena, there is an old service station by the name of Cars on the Route. It was an old service station restored by four Galena women, earning it the nickname Four Women on the Route. Today, in addition to the usual sandwiches and snacks, it is a haven for Route 66 themed arts and crafts.

  • Rainbow Curve Bridge

Almost one hundred years old, the Rainbow Curved Bridge in Baxter Springs and Riverton is the only surviving fixed marsh rainbow arch bridge on Route 66. A stroll on the 130-foot long single lane bridge will give you an opportunity to enjoy the nature around.

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Oklahoma

  • Allen’s Conoco Hole in the Wall

Stopping by Allen’s Conoco Hole in the Wall is like traveling back in time. Its exterior wall is painted bright green with red trim. For many years, it operated as a Conoco fuel and gas station and is rumored to have served gas to infamous law-breaking couple Bonnie and Clyde. Currently, it is a souvenir and gift shop and does not offer gas anymore.

  • The Gateway Sign

Even though it shares a name with a popular beach city in Florida, Miami in Oklahoma could not be any more different. It not only is home to the headquarters of nine Native American tribal nations, but it is also the Route 66 city with the longest Main Street. It has a large Gateway to Route 66 sign too that greet visitors that enter it.

  • Ribbon Road

Tucked in a quiet part of Ottawa County, a nine-foot wide paved sidewalk called Ribbon Road exists. First laid out in the early 1920s, it runs between Miami and Narcissa as part of Route 66 and continues as Oklahoma Highway #7 as you go south.

  • Ed Galloway’s Totem Pole Park

Thinking of taking a quick detour? Ed Galloway’s Totem Pole Park is four miles off of Route 66 and is well-worth a peek.  Sitting on a vast 14 acres of land, it only has a 12 structures standing, including a 90-foot tall totem pole decorated with hundreds of brightly colored Native American emblems. It also features the Fiddle House, which is an eleven-sided building with concrete totem poles supports.

  • Pryor Creek Bridge

If you are up for another detour, visit the Pryor Creek Bridge. Built in 1926, it is an old section of Route 66 and the only remaining Modified Pratt Through Truss designed bridge in the state. It is 123-foot long and is only open to pedestrians.

  • The Blue Whale

Given as a wedding anniversary gift, a giant blue whale statue sits in a small pond in Catoosa. It was made by a man named Hugh Davis who wanted to surprise his wife Zelta.  One of the most recognizable Route 66 attractions, it is made out of concrete and pipe and is 80-foot-long. Today, the site also has a picnic area and a souvenir and concession shop.

  • Davenport

Situated on the “Curve” of Route 66, Davenport is a small but bustling town renowned for its Brick Paved Broadway Street and Magnolia and Texaco Service Stations, all of which were built between the mid-1920s and early 1930s. It is also home to Route 66’s tallest mural, which you can find on the south face of the Farmers Bank Building.

  • Milk Bottle Grocery

If you think you’ve seen all the eccentricity Route 66 has to offer, Oklahoma City has one more. The 1930-constructed Milk Bottle Grocery is a triangular-shaped building with a large milk bottle affixed on top of its roof.

  • National Route 66 Museum

To listen to the stories of those who traversed the Mother Road way before you, go to the National Route 66 Museum in Elk City. The museum features murals, historical documents, and other memorabilia that tell the story of Route 66 from its inception.

  • Oklahoma Route 66 Museum

In Clinton, you can go for another museum stop and check out the Oklahoma Route 66 Museum. It offers a vast collection of artifacts, including a 14-foot-tall kachina doll, and a virtual walking tour of Route 66 for more in-depth learning.

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Texas

  • Phillips 66 Gas Station

Said to be the most photographed landmark on all of Route 66, the Phillips 66 Gas Station in McLean is a vintage building, one of the oldest Phillips 66 stations in the state. With bright orange pumps, red roof, and painted-on glass and windows, it looks fun and a bit cartoonish.

  • Amarillo

As the most important city on Texas Route 66, Amarillo offers enough places and activities for a day or two. It has the Cadillac Ranch, an extraordinary attraction where ten Cadillac cars covered with colorful graffiti are half-buried nose-first in the ground. It also has the Route 66 Historic District, which has more than one mile of historic buildings that now house restaurants, bars, stores, and art galleries.

  • Glenrio

If you come from a big city, you might find a visit to the ghost town of Glenrio quite interesting. Although the Route 66 era buildings in this abandoned vastness are no longer operational — the post office, service station, motel, café, and a dozen others — it still attracts many curious motorists.

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New Mexico

  • Tucumcari

As you pass the Texas-New Mexico border, Route 66 leads you to Tucumcari. Vibrant and active, this city gives off an old western vibe — with the traditional pueblo-style architecture of its vintage motels, restaurants, and service stations. Many of these business establishments feature electric neon signage too. For Route 66 history enthusiasts, the Blue Swallow Motel, Tee Pee Curios, Route 66 Monument, New Mexico Route 66 Museum, and Murals of Tucumcari are highly recommended.

  • Santa Fe

As the capital city of New Mexico, Santa Fe has a reputation for rich history and excellent art. Even though it only comprised a short segment of Route 66, it still has several attractions worthy of a visit. At the top of the list are the La Fonda Hotel, Museum Hill, New Mexico History Museum, and Santa Fe Plaza.

  • Albuquerque Central Avenue

During the heyday of Route 66, tourism in Albuquerque boomed. Hordes of restaurants, motels, souvenir shops, and other businesses sprang up, particularly on Central Avenue, to accommodate the increasing number of pilgrims. There’s the 66 Diner, Zia Motor Lodge, KiMo Theatre, and Sandia Peak Aerial Tramway just to name a few.

  • El Rancho Hotel and Motel

Curious about where the biggest stars of the Hollywood Golden Era stayed while in New Mexico? Founded as a railhead city, Gallup was a top filming location for Hollywood Westerns in the 1940s and 1950s because of its proximity to rugged terrain. The El Rancho Hotel and Motel, in particular, hosted Katharine Hepburn, Humphrey Bogart, John Wayne, and many other stars. Today, you can enjoy local cuisine there, stay overnight, or do a tour of the grand lobby.

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Arizona

  • Wigwam Village Motel #6

It is not often that you get a chance to spend the night in a wigwam. In Holbrook, you can stay at the Wigwam Village Motel #6 and find out what it is like to sleep in one of these 28-foot high white teepees. Equipped only with a bed, bathroom, and fan/heater, the amenities may be limited but the aficionados will definitely appreciate this roadside accommodation that celebrates Southwestern culture and the historic route.

  • Grand Canyon National Park

Although not exactly on Route 66, the Grand Canyon National Park is only a short drive from either Flagstaff or Williams, two cities on the edge of the Mother Road. Thus, it only makes sense to make a stopover at one of the seven natural wonders of the world. The steep, jagged gorge stretches across 227 miles, and offers breathtaking views of the rocky terrain and the Colorado River.

  • Seligman

Called the Birthplace of Historic Route 66, Seligman used to be a railroad town. It was a favorite stopping spot by westbound travelers passing by Arizona back in the day. Today, one of the most popular places to visit here is Angel & Vilma’s, which is a gift shop. Other highlights in the city are the Snow Cap Diner, Historic Seligman Sundries, yellow Edsel taxi, and Route 66 Motoporium.

  • Historic Peach Springs Trading Post

A town in the Hualapai Indian Reservation, Peach Springs is home to the Historic Peach Springs Trading Post. It is a 1917 Pueblo Revival-style building that used to operate as a store and post office and currently serves as the office of the Hualapai Tribal Forestry, Wildlife Conservation, and Game and Fish.

  • Hackberry General Store

Outside, the Hackberry General Store in Hackberry may look rusted and rundown. But once you get inside, this former gas station and garage transports you to another world. Vintage license plates, patches from all over the world, retro furniture and décor, and Route 66 artworks fill its interior.

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California

  • Needles

As you enter the Californian border, your first stop will be Needles. With summer temperatures of over 105 degrees F, it is the hottest town in the country. It is also Route 66’s Gateway to California, with a plethora of vintage motels and motor inns, such as the Route 66 Motel and the El Garces Hotel.

  • Essex

The drive leading to Essex and onwards will probably be one of the toughest parts of the entire trip. Not only will the weather be hot, the roads will be steep and hazardous too. But do not let these prevent you from seeing more of Route 66. In Essex, you can find the old post office and the ruins of the Wayside Cafe. You can also visit the Water Well where you can get water for free.

  • Roy’s Motel and Café

Founded in 1938, Roy’s Motel and Café started out as a gas and service station in the Amboy segment of the Main Street of America. It was refurbished in 2008 and is now the only business operating in town.

  • San Bernardino

What about spending another night in a teepee? San Bernardino has a Wigwam Motel too. Also around the city, there are more Mother Road sites you can visit, such as the McDonald’s museum, the site of the first ever McDonald’s restaurant built in 1940, and the historic Santa Fe Railway Station and Depot that was opened in 1918.

  • Santa Monica Pier

As your drive along Route 66 gets closer and closer to the ocean, this means you are nearing the western terminus of the route. In Santa Monica, the official western terminus of the legendary road is found at Santa Monica Pier. It is marked by a prominently displayed End of Trail sign.

For completing the trip, there’s no better way to celebrate than to see more classic Route 66 sites in the area, such as the Hotel California, Santa Monica Motel, and the 1960s Wilshire Service station. If you have more time, going to the Community Brake and Speedometer Service Inc., a garage that opened in 1926, and the Miller Motor Hotel Apartments, a vintage motel, is also highly recommended.


Hope you’ve enjoyed this look into Route 66. If you do take up this road trip, send photos! Would love to discover this amazing road trip from your perspective.

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