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The Ultimate Route 66 Road Trip Itinerary

The Ultimate Route 66 Road Trip Itinerary

This Route 66 road trip itinerary includes everything you should see and do on your journey, including day trips and the best things to do on Route 66.

If you’re planning a cruise down Route 66, America’s iconic Mother Road, you’ve got an opportunity to relive a piece of important American history that stretches over 2,400 miles and nearly six decades into the past.

In this article, we’ll take a tour of some of Route 66’s iconic landmarks and road stops, as well as offer some tips for making the most of your road trip experience. So, buckle up and get ready to explore!

Fun Facts About Route 66

  • Route 66 starts in Chicago, Illinois, and continues until Santa Monica, California – unless you’re driving it the opposite way around!
  • Technically, Route 66 was begun in Chicago as a way to bridge the East Coast to the West Coast, so starting in Chicago gives you the most historically accurate timeline.
  • You’ll pass through a total of eight different states – Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and finally California.
  • While Route 66 has been replaced by the Interstate Highway System for official purposes, you can still follow the historic route using old maps and road signs, as well as modern apps that help you locate gas stations along the way, and local places to eat.
  • Although many of Route 66’s historical gas stations are no longer in service, there are still plenty of pit stops, eateries, and roadside attractions that keep the spirit of the old road alive.

Route 66 Road Essentials: What to Pack

Be warned that a full Route 66 trip is a 10-to-12 days driving experience, if you’re planning to see all the sights and make frequent stops. This means you should pack for multiple weather conditions, vehicle maintenance, and personal comfort.

If you’re just legging it the whole way through, you can make the trip in about 3 to 4 days.

Get a quick routine maintenance check done on your vehicle to ensure it’s up for the trip, and do a little shopping for spare accessories for trucks (or cars, or motorcycles) to avoid any “it’s 50 miles walk to the next service station” scenarios.

Finally, the latter parts of Route 66, such as Arizona and New Mexico, involve a bit of desert driving. Make sure you’ve got a trunk full of water bottles, and unless you’re planning on a serious driver’s tan, bring sunscreen as well.

The Ultimate Route 66 Road Trip Itinerary

10 things you have to do in chicago

Section 1 – From Chicago to Oklahoma

Driving straight time: 12 to 13 hours.

Chicago, Illinois: Kick off your trip at Grant Park and snap a picture at the “Begin Route 66” sign.

There are plenty of fun things to do in Chicago to keep the whole family busy. We recommend starting with a trip to Wrigley Field before heading up Willis Tower and then crossing the road to try deep-dish pizza at Giordano’s.

Beyond Chicago, the Cozy Dog Drive-In in Springfield offers travelers a taste of classic American cuisine with its invention of the “hot dog on a stick.”

In Illinois, alongside Grant Park and the “Begin Route 66” sign, don’t overlook Joliet’s historic Rialto Square Theatre for a glimpse of stunning architecture.

Continuing southward to Pontiac, visit the Route 66 Association Hall of Fame & Museum which hosts vintage vehicles and memorabilia.

Further on, Dwight’s Ambler’s Texaco Gas Station showcases restored service stations reminiscent of the heyday travel era.

Wilmington, Illinois: Don’t miss the “Gemini Giant,” a beloved roadside giant standing guard outside the Launching Pad Drive-In.

Check out Cuba’s Wagon Wheel Motel — one of the longest continuously operating motels on this route. Cuba also offers murals celebrating local history lining its streets.

Further west in Rolla, The Totem Pole Trading Post is Missouri’s oldest original business still operating along old Route 66; it provides classic souvenirs.


Stop at Uranus Fudge Factory in St. Robert for some sweet treats (and quirky humor). Springfield itself presents fantastic dining options such as Steak ‘n Shake with roots dating back to Route 66’s golden years.

St Louis arch best places to visit in Missouri

St. Louis: Moving into Missouri, Meramec Caverns in Stanton provide an underground adventure beneath the rolling Ozark hills. These natural limestone caves offer rich historical tours detailing their use as hideouts during wars and by notorious outlaws like Jesse James. Take a slight detour to visit the iconic Gateway Arch; it symbolizes westward expansion. 

Entering Kansas:

Moving forward to Kansas, despite its short 13-mile stretch on Route 66, Galena charms visitors with restored mining-era buildings. Notably (and certainly unmissable), Cars on the Route highlights restored vintage vehicles inspired by characters from Pixar’s movie “Cars.”

Riverton provides Eisler Brothers Old Riverton Store which has operated since 1925 (stock up on snacks).

Baxter Springs: Check out the Rainbow Bridge on Old Route 66 – one of the few remaining Marsh arch bridges.

When you arrive in Oklahoma, embrace more historic charm:

Catoosa: The Blue Whale is an unmissable quirky landmark worth stopping for photos.

Tulsa: Explore preserved segments of original Route 66 pavement that tell tales of many travelers before you.

Sapulpa features Rock Creek Bridge from ’26 carrying traffic until ’58, providing a nostalgic walk over the original structure. In Tulsa, visit the Meadow Gold Sign, restored to its neon glory as a beacon of Route 66 history.

Each landmark presents its own unique story and adds depth to your understanding of this legendary highway as more than just asphalt – it’s an embodiment of American history and culture.

Section 2 – From Oklahoma to New Mexico

Driving straight time: 7 to 8 hours.

Transitioning from Oklahoma into New Mexico, the middle segment of Route 66 offers an intriguing blend of cultural history and striking landscapes.

Continuing our journey from Oklahoma to New Mexico, travelers will encounter not only a shift in terrain but also an engaging mix of historical and cultural artifacts.

Stroud offers an authentic dining experience at the Rock Café (operating since 1939), known for delicious meals and its historic ambiance.

Heading towards Arcadia, make sure to stop by POPS—a modern roadside attraction with hundreds of soda flavors and a towering soda bottle sculpture that lights up brilliantly at night.

Vinita hosts Clanton’s Café famous for chicken fried steak serving travelers since ’27.

Nearby Foyil boasts Ed Galloway’s Totem Pole Park displaying hand-carved structures towering over visitors.

As you depart Oklahoma City, consider stopping at the Museum of Osteology, which holds fascinating insights into the skeletal systems of various species.

Oklahoma City

Visit 9 for extensive exhibits on cowboy culture and Native American artifacts. Further west in Clinton, The Oklahoma Route 66 Museum takes visitors through different eras of America’s Mother Road with interactive displays.

Hydro’s Lucille’s Service Station remains an enduring symbol of classic hospitality from the road’s earlier days. Lastly before crossing into Texas: 

Elk City has another significant museum—The National Route 66 Museum Complex—providing insights into various state-specific histories tied together by this iconic highway.

Oklahoma City, Oklahoma: Explore the historic stockyards and visit the insightful National Cowboy & Western Heritage Museum.

Cadillac Ranch Texas Route 66 USA Bucketlist

Crossing into Texas:

Amarillo offers more than just Cadillac Ranch. The Big Texan Steak Ranch challenges visitors with its legendary 72-ounce steak dinner, free if you can eat it all in one hour. Could you manage that? 

Expand your visit to Amarillo with a stop at the American Quarter Horse Hall of Fame & Museum, which delves into the history and impact of these majestic animals on Western culture.

As Route 66 meanders through Amarillo, take note of how the city integrates modern culture with historic elements. Swing by Historic Sixth Street for antique shops and classic architecture showcasing mid-20th-century design.

Driving from Texas to Mexico

In Adrian (the geographic midpoint of Route 66), relax at Midpoint Café where their “ugly crust” pies are a traveler’s delight—a must-try dessert after hours on the road.

Vega’s Magnolia Station stands restored as a museum showcasing travel relics and historical artifacts from Route 66’s heyday. Additionally, check out Dot’s Mini Museum filled with an eclectic collection celebrating local history along America’s Main Street.

Glenrio straddles the Texas-New Mexico border:  

Once a bustling stop for travelers, this ghost town now serves as a haunting reminder of how highways evolve and change over time.


New Mexico:

Tucumcari, New Mexico: Known for its neon signs and retro motels like the Blue Swallow Motel which epitomize classic Route 66 nostalgia. 

Enhance your journey through Tucumcari’s historical district. Spend more time inspecting murals vividly depicting mid-20th-century life along Route 66; these are snapshots frozen in time speaking volumes about community pride and artistic expression back then.

Santa Rosa houses The Blue Hole, a popular spot for divers exploring underwater caverns. Its crystal-clear waters provide a perfect respite amidst the arid landscape. This hidden gem invites adventure enthusiasts to discover its natural beauty and tranquility.

Santa Fe Loop (optional detour): This older route takes you through Santa Fe, where Pueblo-style architecture dominates. It’s a scenic drive offering rich cultural experiences and historical landmarks.

Spend more time inspecting murals that vividly depict mid-20th-century life along Route 66. These snapshots in time speak volumes about community pride and artistic expression from that era.

Breaking Bad locations in Albuquerque

Albuquerque: Known for its annual International Balloon Fiesta; which needs to be on your USA bucket list. Take time to stroll along Central Avenue to see preserved sections of Route 66 complete with vintage neon signs. You can also see some of the Breaking Bad TV Series locations!

This leg combines a rich mix of Americana with unique natural backdrops – ensure your camera is ready to capture these unforgettable sights!

Section 3 – New Mexico to Santa Monica

Driving straight time: 11 to 12 hours.

As you venture from New Mexico towards Santa Monica, the final stretch of Route 66, expect a dramatic change in scenery as the desert landscapes give way to coastal views. This portion of your journey is ripe with historical and cultural sites.

Petrified Forest National Park, Arizona: A must-visit for its colorful fossilized trees and panoramic desert views. Explore the Rainbow Forest Museum, where you can learn about prehistoric life and view exhibits featuring petrified wood specimens.

Holbrook’s Wigwam Motel offers a quirky lodging experience that embodies mid-century Americana with its unique teepee-shaped rooms—a fun photo op and an unforgettable stay.

Grand Canyon National Park

Flagstaff, Arizona: Consider a side trip to the Grand Canyon, an awe-inspiring natural wonder only about 80 miles north. Flagstaff itself boasts Lowell Observatory where Pluto was discovered; it provides fascinating stargazing opportunities against clear skies (ideal for astronomy buffs).

Continuing through Arizona, don’t skip Kingman: Visit the Historic Powerhouse Visitor Center which doubles as Arizona’s dedicated Route 66 museum. It provides rich insights into the road’s history and local culture.

Winslow: Famously immortalized by The Eagles’ song “Take It Easy”, this town invites you to pose beside ‘the standing man’ statue. It’s a nostalgic spot and offers countless Instagrammable moments!

Seligman: Known as the birthplace of Historic Route 66’s revival, Seligman is perfect for those wanting to experience vintage Americana. Enjoy its retro diners, colorful murals, and unique shops that capture the spirit of mid-century travel.

California road trip tips

Crossing into California

Needles: Explore remnants of Old West history before heading deeper into your California road trip. Check out the El Garces Harvey House, an architectural marvel that once served as a key railroad stop.

Barstow: Stop at the Route 66 Mother Road Museum located in the historic Casa del Desierto train station. This museum features fascinating exhibits on the road’s history and its impact on American culture.

Victorville: Visit the California Route 66 Museum showcasing various nostalgic artifacts and photographs. It’s a perfect place to delve deeper into Route 66 lore.

San Bernardino: Don’t miss San Bernardino’s First Original McDonald’s Site & Museum, which offers memorabilia from one of America’s most iconic fast-food chains (a must-see for fast-food enthusiasts).

Santa Monica, California: The end of the trail. Celebrate your arrival at Santa Monica Pier where historic Route 66 officially ends.

This part of Route 66 showcases everything from desert vistas to coastal views, capturing the full range of iconic scenes along the historic highway as you approach Santa Monica.

As you reach Santa Monica and reflect on your journey from Chicago, each mile on Route 66 has offered unique insights into America’s cultural and historical landscape.

From the bustling streets of Chicago to the serene beaches of California, you’ve traversed a living museum filled with diverse attractions, rich history, and iconic landmarks.

Traveling Route 66 is more than just a road trip; it’s an immersion into the heart of America’s story. Its progress, dreams, and resilience. This legendary highway remains a testament to the spirit of adventure that continues to captivate travelers worldwide.

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ULTIMATE California Bucket List - Creative Travel Guide

Wednesday 29th of May 2024

[…] After exploring the pier, take a walk along the Santa Monica beach and enjoy some sunbathing, swimming, and beach volleyball. This is also the end of the iconic Route 66 drive! […]

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