Announcement:
Route 66 Traditional Trail (was Centennial)
Route 66 road trip holiday including the Grand Canyon
Designed specifically for the 100 year anniversary, this self drive road trip will take you along Route 66 from Chicago to Los Angeles through 8 US states and includes cities such as St Louis, Oklahoma City, Amarillo and Santa Fe. A side trip to the fabulous Grand Canyon is included. Las Vegas was never part of Route 66, so this isn’t part of this itinerary - you’ll go through Oatman and the Black Mountains instead. However Las Vegas can be added as a side trip if you wish.
This is real Route 66 and we mix modern hotels with historic accommodation such as the Wigwam Motels. If you want an authentic Mother Road experience, this is the trip for you.
Remember: We’re UK-based, and every holiday we create is fully flexible – you can add nights, upgrade hotels, or enhance your itinerary. We love designing tailor-made self-drive adventures just for you!
22 night self drive holiday from £2,799pp including flights
Highlights
Epic 2500 mile road trip from Chicago to Los Angeles
See St Louis from the top of the historic Gateway Arch
Keep to the historic route as much as possible with a small detour to the mighty Grand Canyon
Get a photo at Santa Monica Pier’s “End of the Trail” sign
Your itinerary
DAYs 1-3: ARRIVE and explore CHICAGO
Begin your Route 66 holiday in Chicago. Explore the Windy City’s Magnificent Mile, Willis Tower, and live music before your road trip.
Your Route 66 adventure begins in Chicago, Illinois, the vibrant city where the Mother Road officially starts. Capture your first photo at the “Route 66 Begin” sign on Adams Street before exploring the Windy City’s mix of skyline views, lakeside charm, and legendary food — from deep-dish pizza to Chicago-style hot dogs. Spend your days discovering the Magnificent Mile, admiring sweeping panoramas from the Willis Tower Skydeck or 360 Chicago, and visiting landmarks like the Water Tower and Millennium Park’s Cloud Gate (The Bean). Dive into the city’s rich culture at the Art Institute of Chicago or Field Museum, then take an architectural river cruise to see its famous skyline from the water. Evenings are best spent with live blues or jazz, setting the perfect tone for your journey along America’s most iconic highway.
3 Nights in
Chicago, IL
Arrive &
Explore
DAY 4: HEAD TOWARDS PONTIAC
Drive Route 66 from Chicago to Pontiac. See the Gemini Giant, Route 66 murals, and museums celebrating the Mother Road.
Pick up your rental car and begin your Mother Road adventure. Heading south, stop at the quirky Gemini Giant in Wilmington, one of Route 66’s beloved Muffler Men. Pass through small towns dotted with restored gas stations and retro diners before arriving in Pontiac, Illinois. This charming town is famous for its more than 20 colorful Route 66 murals, which make for great photo stops. Visit the Route 66 Hall of Fame and Museum, explore the Pontiac-Oakland Automobile Museum, and step inside Bob Waldmire’s eccentric “Road Yacht,” a converted school bus that’s become a legend of the road. Spend the evening soaking in the nostalgic atmosphere of Pontiac.
1 Night in
Pontiac, IL
100 miles
DAY 5: SPRINGFIELD, IL
Travel Route 66 to Springfield, Illinois. Explore Lincoln’s Home, the State Capitol, and the Route 66 Experience exhibit.
Continue through the Illinois countryside, passing towns like Bloomington and Lincoln, which boast historic courthouses, murals, and diners still serving travellers today. Your destination is Springfield, Illinois, a city steeped in American history. Walk through Lincoln’s Home National Historic Site, where the 16th President lived before moving to the White House. Tour the Illinois State Capitol and explore the Illinois State Fairgrounds, home to a fascinating Route 66 Experience exhibit.
1 Night in
Springfield, IL
105 miles
DAY 6: ST LOUIS & GATEWAY ARCH
Journey to St. Louis on Route 66. Drive original brick road, visit Ariston Café, walk the Chain of Rocks Bridge, and see the Gateway Arch.
Today’s drive takes you just 100 miles to St. Louis, crossing from Illinois into Missouri. Along the way, drive a preserved section of original brick Route 66 in Auburn, then stop in Litchfield to dine at the historic Ariston Café, one of the oldest restaurants on Route 66. As you reach St. Louis, make time to walk across the Chain of Rocks Bridge, once an important crossing for Route 66 travelers over the Mississippi River. End your day at the soaring Gateway Arch, America’s tallest monument and a symbol of the “Gateway to the West.” The lively dining and music scene downtown makes for a perfect evening.
1 Night in
St Louis, MO
100 miles
DAY 7: BIRTHPLACE OF ROUTE 66
Drive Route 66 through the Ozarks to Springfield, Missouri, birthplace of Route 66. Visit murals, diners, and the Route 66 Car Museum.
Leaving the urban skyline behind, today’s drive winds into the scenic Ozark Mountains. Stop in Cuba, Missouri, the “Route 66 Mural City,” where hand-painted murals tell stories of local history. Continue through small towns like Rolla, filled with vintage service stations and roadside diners, before reaching Springfield, Missouri. Known as the Birthplace of Route 66, it was here in 1926 that officials first designated the highway. Visit the Route 66 Car Museum, explore retro neon signs, and enjoy the lively downtown atmosphere.
1 Night in
Springfield, MO
215 miles
DAY 8: CARTHAGE & RED OAK II
Visit Carthage and Red Oak II on Route 66. Explore this recreated town of gas stations, stores, and Americana charm.
Today’s drive is short but packed with history. Arrive in Carthage, Missouri, a town with beautiful historic architecture and a classic courthouse square. Just outside of town, explore Red Oak II, an open-air museum created by artist Lowell Davis. Here, historic gas stations, general stores, and homes have been relocated and restored to create an entire Route 66 ghost town brought back to life. Stroll the quiet streets and imagine life in a mid-20th-century small town. Carthage and Red Oak II perfectly capture the nostalgic Americana that makes Route 66 unforgettable.
1 Night in
Carthage, MO
60 miles
DAY 9: TULSA
Drive through Missouri, Kansas, and into Oklahoma on Route 66. See the Blue Whale of Catoosa and arrive in Tulsa.
Today you’ll cross three states in one day! After leaving Missouri, you’ll enter Kansas for a short but memorable 13-mile stretch of Route 66 that includes the restored Kan-O-Tex Service Station in Galena and the Rainbow Bridge in Riverton. Next, cross into Oklahoma and stop at the quirky Blue Whale of Catoosa, one of the most photographed icons on the route. End the day in Tulsa, a city filled with art deco architecture, Route 66 neon signs, and a vibrant live music scene.
1 Night in
Tulsa, OK
130 miles
DAY 10: OKLAHOMA!
Travel Route 66 to Oklahoma City. Drive the Sidewalk Highway, see diners and motels, and explore Bricktown.
Continue your road trip deeper into Oklahoma, where Route 66 history comes alive. Drive the amazing Sidewalk Highway between Miami and Afton, a nine-foot-wide original stretch of road that shows how Route 66 once looked. Pass through towns lined with retro diners and motels before reaching Oklahoma City. Here you can explore the lively Bricktown Entertainment District, visit the National Cowboy & Western Heritage Museum, or enjoy a meal at a classic steakhouse. Oklahoma’s warm hospitality and rich heritage make this leg a real highlight of your Route 66 journey.
1 Night in
Oklahoma City, OK
115 miles
DAYs 11-12: AMARILLO, TEXAS
Drive Route 66 into Texas. Visit Clinton’s Route 66 Museum, Shamrock’s U-Drop Inn, and Cadillac Ranch in Amarillo.
Journey across the wide-open plains into the Texas Panhandle, where the spirit of the Old West meets Route 66 nostalgia. Stop at the Route 66 Museum in Clinton to trace the story of America’s Main Street, then admire the art deco U-Drop Inn in Shamrock before rolling into Amarillo. Here, the legendary Cadillac Ranch awaits — a surreal lineup of brightly painted cars half-buried in the desert, inviting visitors to leave their own mark. Settle in for two nights to experience true Texas hospitality, from cowboy charm to hearty steaks. Spend your full day exploring Palo Duro Canyon State Park, the awe-inspiring “Grand Canyon of Texas,” with its red cliffs and winding trails. Back in Amarillo, wander vintage shops, Route 66 diners, and neon-lit streets — the perfect mix of rugged adventure and Americana nostalgia.
2 Nights in
Amarillo, TX
260 miles
DAY 13: TUCUMCARI, NM
Reach the midpoint of Route 66 in Adrian, visit Glenrio ghost town, and stay in neon-lit Tucumcari.
Today you’ll reach the official midpoint of Route 66 in Adrian, Texas, where a photo at the Midpoint Café sign is a must. Continue west, passing the ghost town of Glenrio, straddling the Texas–New Mexico border, before arriving in Tucumcari. This classic Route 66 town is famous for its neon-lit motels, vintage signs, and more than 30 colorful murals. Overnight in one of several historic motels where the glow of neon perfectly captures the 1950s spirit of Route 66.
1 Night in
Tucumcari, NM
115 miles
DAY 14: SANTA FE OR ALBUQUERQUE
Drive Route 66 to Santa Fe or Albuquerque. Experience New Mexico culture, adobe architecture, and even Breaking Bad filming spots.
From Tucumcari, you can follow the original 1926 alignment to Santa Fe, a city of adobe architecture, art galleries, and historic charm, or take the later realignment directly to Albuquerque. In Santa Fe, explore the historic plaza and art scene, while Albuquerque offers a mix of Old Town charm and pop-culture sites like Breaking Bad filming locations. Whichever route you choose, you’ll experience New Mexico’s unique blend of Native American, Hispanic, and Western culture.
1 Night in Santa Fe or
Albuquerque, NM
115 miles
DAY 15: GALLUP
Travel Route 66 west to Gallup. Cross the Continental Divide, see historic motels, and explore Native American trading posts.
Drive west through New Mexico, passing towns filled with diners, motels, and gas stations that once welcomed cross-country travelers. Stop for lunch in Grants or explore lava fields at El Malpais National Monument. Cross the Continental Divide, a geographic highlight of your road trip, before arriving in Gallup. Known for its Native American trading posts and historic hotels, Gallup has long attracted Hollywood stars and travellers alike. Spend the evening soaking in the town’s cultural heritage.
1 Night in
Gallup, NM
200 miles
DAY 16: PETRIFIED FOREST NP
Visit Petrified Forest and Painted Desert before arriving in Winslow, Arizona for a photo “Standin’ on the Corner.”
Cross into Arizona today and visit the stunning Petrified Forest National Park and Painted Desert, where colourful landscapes and fossilised trees tell the story of prehistoric times. Continue to Winslow, immortalized in the Eagles’ song Take It Easy. Pose for a photo at the “Standin’ on the Corner” park, a favourite Route 66 stop, and enjoy the small-town atmosphere surrounded by history and music.
1 Night in
Winslow, AZ
130 miles
DAY 17: GRAND CANYON
Leave Route 66 at Flagstaff for the Grand Canyon South Rim. Experience sunset views and stunning landscapes.
Today you’ll temporarily leave Route 66 at Flagstaff to head north toward one of the world’s greatest natural wonders — the Grand Canyon. Stay near the South Rim, where sunset paints the canyon walls in breathtaking colours. Explore scenic viewpoints, hiking trails, and the historic Grand Canyon Village. This detour is one of the most awe-inspiring highlights of the entire road trip.
1 Night in
Grand Canyon, AZ
140 miles
DAY 18: KINGMAN
Drive from the Grand Canyon through Williams and Seligman to Kingman. Visit Hackberry and stay in a retro Airstream.
Rise early to witness sunrise over the Grand Canyon before rejoining Route 66. Drive through Williams, a lively Route 66 town, and stop in Seligman, known for its quirky shops and being the birthplace of historic Route 66. Visit the nostalgic Hackberry General Store, a time-capsule of Route 66 history, before arriving in Kingman. Tonight, you’ll stay in a stylish retro Airstream trailer, a unique experience that embodies the spirit of the open road.
1 Night in
Kingman, AZ
170 miles
DAY 19: THE BLACK MOUNTAINS
Travel Route 66 through Oatman, Arizona, and into Needles, California. Meet wild burros in this classic mining town.
This section of the road is one of the most scenic. Explore historic downtown Kingman before taking the winding road through the Black Mountains into Oatman, an old mining town famous for its wild burros roaming the streets. Cross into California and arrive in Needles, a desert town that has welcomed Route 66 travellers for decades.
1 Night in
Needles, CA
70 miles
DAY 20: CALIFORNIA DESERT
Drive Route 66 across the Mojave Desert. Visit Roy’s in Amboy, the Route 66 Museum, and stay in a wigwam motel.
Journey across the Mojave Desert, where ghost towns and abandoned motels tell the story of Route 66’s golden age. Stop at the iconic Roy’s Motel & Café in Amboy, one of the most photographed spots on the route. Continue through Barstow and Victorville, home to the California Route 66 Museum, before reaching San Bernardino. Tonight, you’ll experience a true piece of Americana by staying in a classic concrete wigwam motel.
1 Night in
San Bernardino, CA
250 miles
DAYs 21-22: END OF THE TRAIL
Complete your Route 66 road trip at the Santa Monica Pier. Celebrate at the “End of the Trail” sign and explore Los Angeles and Beverly Hills
Your epic Route 66 journey ends in Los Angeles, where palm-lined boulevards lead you to the Santa Monica Pier — the official “End of the Trail.” Capture the perfect photo at the sign, stroll along the beach, or ride the historic carousel as the Pacific sparkles before you. Spend two nights soaking up the glamour of LA: explore Beverly Hills and Rodeo Drive, hike to the Hollywood Sign, or take in sweeping city views from the Griffith Observatory. Film lovers can trace movie history at famous locations from Back to the Future, Grease, and Duel, while shoppers and sunseekers alike will find plenty to enjoy. On your final morning, sip coffee by the ocean or browse Santa Monica’s boutiques before returning your car and heading home — filled with unforgettable memories of your once-in-a-lifetime Route 66 adventure.
2 Nights in
Santa Monica, CA
70 miles
May- Jun & Sept- Oct: Weather is likely to be pleasant for the entire trip. The midwest shouldn’t be too cold and the southwestern states shouldn’t be too hot.
We would expect maximum temperatures to be in the 20°C - 30°C range in the midwest and 25°C - 35°C in the south and southwestern states
Flight times to/from Chicago is around 8 hours and Los Angeles is approx 11 hours. You’ll drive through 3 time zones. Chicago is 5 hours and Los Angeles is 8 hours behind the UK.
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