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Rediscovering America: A Journey Along the Iconic Route 66

Get ready to hit the road and dive into the ultimate American road trip experience! Route 66, the legendary highway stretching from Chicago to Santa Monica, is calling your name with its mix of stunning scenery, offbeat tourist attractions, and a big dose of retro charm.

Use our itinerary to cover the nearly 2,500 miles from Chicago to California and discover famous landmarks, iconic regional foods, awe-inspiring scenery, and much more on the Main Street of America.

Note: Our guide covers the entire route starting in Chicago, but you can go as fast or as slow as you like to make sure you don’t miss anything along the Mother Road.

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Route 66 Chicago I photo credit: rawf8 / Shutterstock

Getting to Know Route 66

Route 66, the Mother Road, the Main Street of America, or whatever other name you call it was established in 1926. During the Great Depression, Route 66 — called the Mother Road by John Steinbeck in The Grapes of Wrath — became a lifeline for people migrating west in search of opportunities.

The construction of the interstate highway system in the 1950s led to the decline of Route 66, as travelers began using the faster and more efficient interstates. However, its impact lives on in songs, films, restaurants, and museums, and sections of it have been preserved as historic byways.

Chicago, Illinois

Your journey along Route 66 begins in the Windy City, the perfect place to spend your first day exploring. Pretend you’re Ferris Bueller for a day as you explore iconic eateries, well-known landmarks, and plenty of beautiful scenery on the shores of Lake Michigan.

  • Art Institute of Chicago: You can indulge your inner Ferris Bueller by visiting this museum which is home to a massive collection of works, including American Gothic.
  • Millennium Park: Home to the famous Cloud Gate, also known as “The Bean,” visitors are drawn to its unique shape and the mesmerizing reflections it creates.
  • Navy Pier: Situated along the Lake Michigan shoreline, the pier is a lively hub that features a variety of shops, restaurants, and entertainment venues.

RELATED: The Windy City is full of lots of other great landmarks worth seeing including Willis Tower, Wrigley Field, The Magnificent Mile, The Buckingham Fountain, and the Chicago Riverwalk

Where to Eat

  • Pizza: Iconic Chicago deep-dish pizza can be found all over the city at spots like Lou Malnati’s, Gino’s East, George’s Deep Dish, Giordano’s, and many more.
  • Chicago hotdogs: These iconic franks with their plethora of toppings can be enjoyed at Superdawg Drive-In, Wolfy’s, The Vienna Beef Factory Store, Jimmy’s Red Hots, Portillos, and many other spots.
  • Italian Beef: These meaty, gravy-dipped sandwiches can be found at Al’s #1 Italian Beef, Luke’s Italian Beef, Jay’s Beef, Johnnie’s Beef, Mr. Beef on Orleans, and many more.

 To officially begin your Route 66 journey, a historic Route 66 sign is mounted facing traffic on East Adams Street, just west of its crossing with South Michigan Avenue.

Chicago to Springfield, Illinois

Your journey on Route 66 out of Chicago continues about 200 miles southeast to Springfield, the capital of Illinois. History buffs are in luck because Springfield was the longtime residence of U.S. President Abraham Lincoln.

RELATED: The Route 66 Association of Illinois’ Hall of Fame & Museum in Pontiac Illinois is less than two hours northeast of Springfield. It features mementos, photo ops, and travel resources.

  • Abraham Lincoln Presidential Museum and Library: Allows an immersive look into the triumphs and tragedies of the former president and view artifacts that can’t be found anywhere else.
  • Lincoln Home National Historical Site: This is the only home Lincoln ever owned and where he lived from 1844-61. Visitors can take guided tours to get a glimpse into Lincoln’s home life.
  • The Illinois State Capital: The Illinois seat of government allows tours where visitors can see its grand architecture, a dome that rises more than 350 feet, and numerous statues and monuments on its grounds.

Where to Eat

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llinois State Capitol Springfield I photo credit: Photos BrianScantlebury / Shuttestock

Springfield, Illinois to St. Louis

Continuing south and veering slightly southwest, Route 66 travelers will arrive in St. Louis, the Gateway to the West.

  • Historic Ariston Cafe: Start your day with a trip to the historic Ariston Café in Litchfield. Built in 1935, the cafe is the longest-operating restaurant on Route 66 and has largely maintained its character from an older era.
  • The Gateway Arch: As the world’s tallest arch, it has been an iconic St. Louis landmark since it was inaugurated in 1967 and reflects the city’s role in westward expansion. Visitors can take a tram ride to the top of the 630-foot arch to enjoy panoramic views.
  • The St. Louis Zoo: Continue exploring St. Louis with a trip to the St. Louis Zoo, where visitors can enjoy an exciting array of animals, fun attractions like the Zooline Railroad, and fun seasonal events.

RELATED: Stop in Colllinsville, Illinois, about 25 minutes outside of St. Louis to catch a glimpse of the World’s Largest Catsup Bottle, which stands 170 feet tall.

Where to Eat

  • Pappy’s Smokehouse: Pappy’s ribs have been voted some of the best in America and hungry travelers can chow down on burnt ends, ribs, brisket, and other BBQ classics.
  • Ted Drewes Frozen Custard: For over 80 years, Ted Drewes has been dishing up its famous frozen custard with more than a dozen mouthwatering flavors.
  • Monte Bello Pizzeria: Billed as one of the originators of St. Louis-style pizza, Monte Bello serves tasty pies and other Italian favorites.

RELATED: Since you’re already traveling a historic road, travel just north of St. Louis to view the historic Chain of Rocks Bridge on the Mississippi River. Noted for its 22-degree bend in the middle, the bridge was formerly used by drivers on Route 66, but now offers scenic views as a pedestrian walkway.

St. Louis to Springfield, Missouri

Your Route 66 excursion continues southwest deeper into the Show Me State into Springfield, the birthplace of the Mother Road. From the indescribable beauty of the Ozarks to the bustle of a thriving city, Springfield offers plenty to do.

DID YOU KNOW: Springfield is home to one of the last remaining original stretches of Route 66 at Kearney Street and Glenstone Avenue.

  • Meramec Caverns: On the way there, visitors can stop in Sullivan, Missouri to experience the uniqueness of Meramec Caverns, known as Missouri’s Buried Treasure. Visitors can embark on guided tours through the caverns to marvel at the intricate stalactites and stalagmites.
  • Route 66 Car Museum: Springfield is also home to the Route 66 Car Museum, a car enthusiast’s dream that’s dedicated to preserving some of history’s most iconic cars and features a collection of over 100 vehicles.
  • Park Central Square: Visitors keen on seeing as much Route 66 history as possible shouldn’t miss a trip to Park Central Square. This iconic spot is home to the city’s history museum, which details Springfield’s role in Route 66 and the history of the route.

Where to Eat

Steak n’ Shake: Built in 1962, this is one of the chain’s oldest restaurants and is listed on the National Register of Historic Places.

Red’s Giant Hamburg: This eatery pays tribute to the original Red’s on Route 66 and offers burgers, ice cream, fries, and other favorites.

College Street Cafe: This cafe specializes in down-home cooking, making hungry travelers feel like they’re sitting down to a family meal.

Tally's Cafe-Tulsa, Oklahoma
Tally’s Cafe | photo via stepbeyondjohn

Springfield, Missouri to Tulsa, Oklahoma

As adventurers continue through the scenic countryside of Missouri, they’ll eventually cross into Oklahoma and stop in Tulsa. From its iconic Art Deco architecture to the lush green spaces along the Arkansas River, Tulsa offers a blend of urban excitement and natural beauty.

  • Blue Whale of Catoosa: Just outside of Tulsa, pull off in Catoosa for a colorful photo op. The Blue Whale of Catoosa is an iconic Route 66 landmark that measures 80 feet long and 20 feet long.
  • Tulsa’s architecture: Once you’ve arrived in Tulsa, transport yourself back to the days of the Roaring 20s as you explore Tulsa’s iconic Deco District, Visitors can take both self-guided and curated tours as they view historic buildings like the Mayo Hotel and the Philcade Building.
  • Tulsa Zoo: The Tulsa Zoo is a fun stop for some family time. Visitors can marvel at tigers, grizzlies, rhinos, and a fascinating collection of animals, spend time at the Helmerich Playground, and much more.

RELATED: Decopolis, Tulsa’s Art Deco mini museum offers free admission and features collections of Art Deco art and artifacts.

Where to Eat

  • Supertam on 66: Located about 70 miles west of Springfield in Carterville, This Superman Museum/ice cream parlor is the perfect place to cool off while enjoying some Man of Steel memorabilia.
  • Wildflower Cafe: If breakfast is the most important meal of the day, travelers can find plenty of breakfast classics with unique and healthy twists.
  • Tally’s Cafe: Journeyers looking for cozy diner vibes will find them here in a place that serves breakfast all day, sandwiches, burgers, country-fried steak, and more.

Tulsa’s River Parks offer a plethora of outdoor fun for travelers of all ages.

Tulsa, Oklahoma to Oklahoma City

The next stretch of your Route 66 journey involves a short jaunt across Oklahoma from Tulsa to Oklahoma City. OKC is a dynamic metropolis that seamlessly blends modern urban amenities with a rich Western heritage, featuring iconic landmarks and plenty of entertainment and dining options.

  • Oklahoma’s Route 66 Museum: On the way to Tulsa, soak up more Route 66 history at the Route 66 Museum in Clinton. The museum offers visitors a fascinating look at the Mother Road, including images, ideas that formed the route, and myths surrounding it.
  • OKC’s Bricktown District: Once you’re in OKC, treat yourself to dinner and a show. The best place to do that is in Oklahoma City’s famous Bricktown district, which has been revitalized into a thriving entertainment destination. Visitors can explore a variety of restaurants, bars, and shops housed in charming red-brick buildings.
  • Local breweries: OKC is also known as a craft beer hotspot and visitors of legal age can traverse the city’s popular Ale Trail, which features more than a dozen breweries, each with their own unique beers.

Where to Eat

  • Rock Cafe: Located about an hour east of OKC in Stroud, Rock Cafe has stood tall since the heyday of Route 66. Visitors can enjoy diner favorites on a griddle that’s been “seasoned for eternity.”
  • Leo’s: If you’re looking for quality BBQ in the heart of Oklahoma, Leo’s is the place for ribs, hot links, brisket, and more.
  • Sid’s Diner: Famous for its onion-fried burgers, this El Reno eatery is perfect for travelers going through town and hungry for local flavor.
Cadillac Ranch-Amarillo, Texas
Cadillac Ranch | photo via adventuresofmeganandmike

Oklahoma City to Amarillo, Texas

A nearly four-hour drive puts you firmly into the Lone Star State and Amarillo, a vibrant city known for its rich Western heritage and diverse attractions.

Driving through the Texas Panhandle, travelers will encounter the halfway point (yes, you’ve still got a long way to go) of Route 66 in Adrian, just west of Amarillo.

  • Cadillac Ranch: This unique Amarillo attraction features 10 Cadillacs all buried nose down at the same angle as the Pyramids of Giza. It’s open year-round, admission is free and makes a great photo op.
  • Palo Duro Canyon: While it’s a half hour from Amarillo, the country’s second-largest canyon is worth a stop. Even though you’ll pass by the Grand Canyon, Palo Duro is worth a stop to see unique geological features, rugged beauty, and vibrant colors.
  • American Quarter Horse Hall of Fame and Museum: This museum celebrates the history of one of the world’s most versatile horses, through unique sculptures and displays, a reading room, and a theater.

Where to Eat

  • Big Texan Steak Ranch: Serves delicious cuts of meat and is home to the 72 oz Steak Challenge, where customers get the meal free if they can finish a monster steak and sides within an hour.
  • Bracero’s Mexican Bar and Grill: Amarillo’s oldest restaurant is a former Route 66 gas station that serves delicious classic Mexican fare.
  • Downtown Food Truck Park: Vistors looking for a quick bite on the way out of town can stop at one of several food trucks offering a variety of cuisines.

Amarillo, Texas to Santa Fe, New Mexico

The next stretch of your Route 66 endeavor takes you into New Mexico and its capital city. Known for its enchanting Pueblo-style buildings, Santa Fe is a hub for unique art and cultural diversity with Native American, Spanish, and Mexican influences.

  • Santa Fe Plaza: For hundreds of years, this historic plaza has been a central Santa Fe landmark, and the sight of concerts, community events, and more.
  • Palace of the Governors: Situated on the north side of the plaza, the palace is the site of the Museum of New Mexico. It dates back to 1610 and its Spanish-Pueblo Revival Style influenced the city’s architecture.
  • Loretto Chapel: This Santa Fe landmark and its famously mysterious spiral “Miraculous Staircase” capture visitors’ attention as an architectural marvel without nails or a central support.

Related: The Georgia O’Keefe Museum is also located in the Plaza and her home and studio are about an hour northwest in Abiquiu.

Where to Eat

  • Del’s Restaurant: About 90 minutes outside Amarillo, travelers can look for the cow topping the sign for Del’s in Tucumcari, New Mexico, and enjoy a tasty array of Mexican and American dishes.
  • Tomasita’s Restaurant: If you passed on Del’s, enjoy Mexican favorites and tasty margaritas at Tomasita’s, which has earned a reputation as one of the state’s best eateries.
  • La Plazuela at La Fonda: The iconic La Fonda hotel is home to the equally impressive La Plazuela, which offers intimate dining and refreshing twists on Southwest cuisine. 
Route 66 Diner-Gallup, New Mexico
Route 66 Diner | photo via daniel.s.3

Santa Fe, New Mexico to Gallup, New Mexico

Continue for about three hours and nearly 200 miles and you’ll still be in New Mexico on your Route 66 trip. As you drive through the state’s scenic Northern landscapes, you’ll eventually pass right through Albuquerque (but don’t take a left turn there).

RELATED: Albuquerque is famous for its International Balloon Fiesta each October and is also home to the Sandia Peak Tramway, which offers incredible desert views.

  • Acoma Pueblo: Known as Sky City, this is the oldest continuously inhabited city in North America and is about 90 minutes from Gallup. Perched atop a sandstone mesa, the pueblo features traditional adobe dwellings and offers panoramic views of the surrounding desert landscape.
  • Church Rock: Located about 20 minutes outside Gallup, this prominent sandstone formation is a scenic sacred Navajo site that gained attention and was once the site of a major uranium spill.
  • Gallup Cultural Center: The center is a hub for celebrating and preserving the region’s rich cultural heritage. Visitors can enjoy galleries and exhibition spaces that display a wide range of art.

Where to Eat

  • Route 66 Railway Cafe: Travelers looking for a hearty meal can find it at this cafe that serves heaping breakfasts, lunches, and plenty of dinner favorites.
  • Earl’s Family Restaurant: This family-style diner is a longstanding Gallup institution that serves all-day breakfast, dinner specials, and plenty of New Mexican favorites.
  • Genaro’s: Nestled just west of downtown, Genaro’s is a local favorite and serves up tasty New Mexican staples.

RELATED: The Tinkertown Museum, a folk art museum featuring a Jeep decorated in pennies and bottle caps, a hand-carved mini Old West town and more is located in Sandia Park, about a half hour east of Albuquerque.

Gallup, New Mexico to Flagstaff, Arizona

Another 200ish miles west takes you from the edge of New Mexico and straight into northern Arizona in Flagstaff, which was the city with the highest elevation in the heyday of Route 66.

Flagstaff is surrounded by natural wonders including the San Francisco Peaks. It’s also close to Sedona’s red rock formations of Sedona and the marvels of the Grand Canyon.

  • Petrified Forest National Park and Painted Desert: Located about an hour outside Gallup, this 2-in-1 park features Triassic fossils, that represent a millions-of-years-old ecosystem, and a living park where plants and animals have adapted to a demanding environment.
  • Lowell Observatory: Flagstaff is home to the place where Pluto was discovered in 1930. Visitors can learn about astronomy, and peer through telescopes to observe the night sky.
  • Winslow Arizona: The city famously mentioned by The Eagles in Take it Easy is about an hour west of Flagstaff and Standin’ on the Corner Park commemorates the song with a statue of a guitar player.

RELATED: Visit the Flagstaff Visitor Center downtown and ask for the second edition of the Arizona Historic Route 66 passport so you can collect stamps as you travel.

RELATED: The San Franciso Peaks are also about an hour north of Flagstaff, and bus tours are offered to San Francisco Mountain. 

Where to Eat

  • Fat Olives: Pizza fanatics will love this Italian kitchen and pizzeria that serves vera pizza napoletana, a pizza found in Naples and made with imported ingredients.
  • MartAnnes Breakfast Palace: This family-owned eatery serves breakfast, lunch, and dinner, but is perhaps best known for its breakfast, which features classics and local favorites.
  • Mr. Zips: This cozy diner has a retro vibe and invites customers to nosh on Mexican specialties, sandwiches, homemade pies, and more.

RELATED: One of the famous Wigwam Hotels, a motel chain where the rooms take the shape of tipis is located in Holbrook, Arizona, about 90 miles east of Flagstaff.

Route 66 - Arizona
Route 66 – Arizona | photo via thivicci

Flagstaff, Arizona to Grand Canyon National Park

Heading northwest and then due north about 80 miles, you’re Route 66 adventure will eventually lead you to the iconic Grand Canyon and Grand Canyon National Park. The short trip leaves plenty of time to enjoy this awesome natural wonder, which is nearly 300 miles long and thousands of feet deep.

Whether you’ve been here before or you’re a first-time visitor, the awe-inspiring views of this vast canyon, carved by the mighty Colorado River, are indescribable.

  • The South Rim: The South Rim is one of the most visited areas of the park. It includes numerous scenic overlooks, historic buildings such as the El Tovar Hotel, a range of hiking trails, and scenic drives.
  • Hiking the Grand Canyon: Hiking in the Grand Canyon offers a unique and awe-inspiring experience. Hikers can choose from many hikes and trails of varying difficulty and length. Guided hikes are also offered to provide unique insights into the canyon.
  • Grand Canyon Village: This visitor hub offers easy access to trails, historic landmarks, lodging accommodations, and dining and shopping options.

Where to Eat

  • Phantom Ranch Canteen: Located at the bottom of the Grand Canyon, a meal here is a unique experience and visitors must hike to get there. Breakfast and dinner options are offered.
  • El Tovar Dining Room: Looking for a world-class dining experience at the Grand Canyon? You’ll find it here in this historic hotel that offers signature items like Prime Rib hash and Salmon Tostada.
  • Arizona Steakhouse: Situated on the rim of the canyon, this eatery features delicious cuts of meat paired with plenty of local beer and wine selections.

Grand Canyon National Park to Kingman, Arizona

After exploring the ins and outs of the Grand Canyon, hop back in your vehicle, head south, and enjoy scenic Northern Arizona landscapes before you turn west toward Kingman, Arizona.

Kingman is a gateway to numerous attractions and natural wonders and embraces its Route 66 heritage with landmarks, museums, and vintage motels.

  • Seligman: About an hour before arriving in Kingman, you’ll arrive in Seligman, Arizona — a quintessential Route 66 town with vintage motels, diners, and souvenir shops that preserve a hearty slice of Americana.
  • Route 66 Museum: Located in the Powerhouse Building, the museum is another fascinating collection of exhibits, vintage signs, photos, and other pieces dedicated to the history of the Mother Road.
  • Locomotive Park: This park features a historic steam locomotive and railcars, providing a glimpse into Kingman’s railroad history and serving as a tribute to the city’s ties to the railroad industry.

Where to Eat

  • Mr.’s D Route 66 Diner: This old-fashioned diner is loaded with Mother Road memorabilia and serves tasty traditional diner fare.
  • Thai 66: If you’re looking for a different dining option, Thai 66 offers delicious Thai favorites including Pad Thai and tasty chef’s specials.
  • Calico’s: For more than 30 years, Calico’s has served up classic breakfast and lunch offerings and fresh dinner options like fish and steak.
Barstow, California-Route 66
Barstow, California | photo via abessich

Kingman, Arizona to Barstow, California

Heading out of Kingman, you’ll drive a little more than 200 miles through the Mojave Desert — which offers breathtaking vistas of the arid landscape, with its unique rock formations and vast expanses of desert terrain.

You’ll eventually end up in southern California in Barstow, less than 150 miles from the end of your journey.

  • Amboy Crater: About 80 miles outside Barstow, travelers can visit the Amboy Crater, a volcanic cinder cone that rises from the desert floor.
  • Mother Road Museum: Yes, another museum (but you’re traveling for nostalgia anyway). If you’ve been to any of the others, this offers another chance to see even more awesome memorabilia from the heyday of Route 66.
  • Calico Ghost Town and Mining Museum: 20 minutes west of Barstow, the ghost town of Calico invites visitors to see a restored silver mining hotspot that features attractions, historic buildings, and annual events. 

RELATED: About 45 minutes west of Kingman, you can visit the town of Oatman, which is ripped from the days of the Wild West and is famous for the wild burros that wander the streets.

Where to Eat

  • Route 66 Pizza Palace: As you draw closer to the end of Route 66, stop in Barstow for your favorite slice or a loaded sub sandwich.
  • Black Bear Diner: Barstow isn’t big but this friendly diner keeps customers coming back with its cozy atmosphere and big breakfasts, burgers, sandwiches, and tasty desserts.

Barstow, California to Santa Monica, California

Stretch your legs, take a deep breath, and enjoy the final 125 miles of your Route 66 journey from Barstow to Santa Monica. This coastal city is known for its beautiful beaches, shopping centers, and incredible ocean views.

  • Santa Monica Pier: The iconic Santa Monica Pier features an amusement park, an aquarium, a historic carousel, and gorgeous ocean views.
  • Shopping: The Third Street Promenade is a pedestrian-friendly shopping and dining district with a variety of shops. Additionally, Santa Monica Place offers upscale shopping options.
  • Palisades Park: This oceanfront park provides walking paths, green spaces, and breathtaking coastal views, making it a popular spot for strolls and picnics.

RELATED: If you’ve been stopping for photo ops along your journey, make sure to visit the Santa Monica Pier where you’ll find a Route 66 End of the Trail sign.

Where to Eat

  • Rusty’s SM Pier: Celebrate the end of your trip with a seafood feast along the pier. Enjoy the ocean breeze as you dig into lobster, shrimp, and other seafood delights.
  • Burger Lounge: After all those miles, what’s better than a tasty burger creation made with grass-fed beef? With options that include chicken, fish, and plant-based, everyone can order their favorite.
  • Japadog: Hotdogs are as American as apple pie, but this eatery serves up taste Japanese-inspired franks in a variety of delicious combinations. 
Route 66-SS
Route 66 I photo credit: VanderWolf Images / Shutterstock

Embark on a Memorable Journey on Route 66

With our handy itinerary, you can, as Bobby Troup famously sang, “get your kicks on Route 66.” No matter if you’re a foodie, a photographer, an outdoor enthusiast, or you simply love to travel, traversing this nearly 2,500-mile-long road is an exciting, enjoyable, and memorable experience.

Ready to experience the ultimate road trip adventure? Hit the iconic Route 66 and discover a world of vintage diners, quirky roadside attractions, and breathtaking landscapes. Embrace the freedom of the open road and create memories that will last a lifetime.