Route 66 Road Trip: 14-Day Itinerary
When Route 66 began in 1926, it was one of the few highways that cut diagonally across the country. Today, 15 percent of Route 66 is completely gone. It is no longer possible to follow the route uninterrupted from Chicago to Los Angeles. Since its inception, Route 66 has also been realigned at least three times. Some re-alignments were major, such as in New Mexico when the road changed direction, while others shifted the asphalt less than one-eighth of a mile.
This road trip outlines the best way to experience Route 66 today, with detailed navigation notes that generally follow the pre-1930s alignment. There will be times when freeway driving is unavoidable and other options explore later alignments that offer the best variety of sights and attractions. Regardless which alignment you take, avoid following “Historic Route 66” signs if they divert away from the suggested route. These often refer to alignments that lead down rutted dirt paths, dead-ends, or disappointing detours.
Route 66 Itinerary
This two-week itinerary hits the key highlights on the Mother Road and honors the places that have stood the test of time. However, things change quickly on Route 66, so consider prioritizing the mom-and-pop, off-the-wall places—every year more of them are forced to shut their doors due to lack of business. Approaching each major town or city, there are usually Route 66 alignments that bypass the most congested areas; since much of Route 66 was realigned along the interstate, it’s easy to jump on the freeway to get to the next destination quicker. But there are many factors you can’t control: road closures due to weather and construction, businesses that don’t stick to their posted hours, and time to chat with locals and fellow tourists.
Day 1
Chicago to Pontiac (100 Miles)
Day one starts in Chicago. Have lunch at Lou Mitchell’s, then head to Pontiac to see the Route 66 Hall of Fame and walk over one or three of the swinging footbridges. Have dinner at the Old Log Cabin Restaurant and consider staying at the Chateau Hotel in Bloomington, about 30 miles away.
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Day 2
Pontiac to St. Louis (200-225 Miles)
Start the day early and drive southwest about 50 miles along Route 66 to Funk’s Grove to pick up some “sirup.” Have lunch at Ariston’s in Litchfield about 1.5 hours away (102 miles). Head to Staunton, about 15 miles away, to say hello to Rich Henry and his loveable rabbits. In another 20 miles, enjoy dinner at Cleveland-Heath in Edwardsville. From there it’s only 23 miles to St. Louis. Check into the Magnolia Hotel for the night.
Day 3
St. Louis to Springfield (215 Miles)
Have breakfast (or dinner) at the all-night Eat Rite Diner in St. Louis. Spend a couple of hours exploring Union Station or the City Museum. In the afternoon, drive about 80 miles to Cuba, check out the murals, the Wagon Wheel Motel and the World’s Largest Rocking Chair. Head to Springfield, the birthplace of Route 66, spend the night at Springfield’s, Best Western Route 66 Rail Haven (call ahead to book the Elvis Suite).
Day 4
Springfield through Kansas to Tulsa (180 Miles)
Start the day with red-velvet pancakes at Gailey’s Breakfast Café before driving about 75 miles to the Missouri state line at Joplin. Continue for a brief 13-mile jaunt through Kansas before checking out Cars on the Route in Galena and having a quick bite at Angels on the Route in Baxter Springs. From there you cross into Oklahoma, home to some of the best Route 66 attractions.
The Coleman Theater in Miami is 10 miles from the Oklahoma border. Plan to drive the “Sidewalk Highway” between Miami and Afton. This 3-mile, 9-foot wide stretch of 1922 roadbed actually pre-dates Route 66. From Afton, it’s 40 miles to see the Andy Payne statue in Foyil and then another 30 miles to Tulsa, where you’ll spend the night at The Mayo or The Campbell.
Day 5
Tulsa to Oklahoma City (100 Miles)
Have breakfast at Maxxwells, before visiting the Greenwood Cultural Center and John Hope Franklin Reconciliation Park, where you’ll learn the history of one of the worst race riots in U.S. history. Afterwards, head west for 106 miles to Oklahoma City and stop at Pops, a neo-modern gas station and soda nirvana. In Oklahoma City, check out the Gold Dome Building inspired by Buckminster Fuller’s design and spend the night at Skirvin Hilton Hotel or the Aloft. Relax with a blood-orange margarita at the Iguana Mexican Grill then prepare your arteries for onslaught at Ann’s Chicken Fry Steakhouse.
Day 6
Oklahoma City to Amarillo (250-300 Miles)
Head out early and check out the Pony Bridge and drive about 115 miles to the Texas state line. The beautifully restored Tower Station and U-Drop Inn Cafe in Shamrock should be your first stop. Drive about 20 miles to McLean and tour the Devil’s Rope Museum. Have lunch at the Red River Steakhouse. Head 70 miles to Amarillo and stay overnight at the Courtyard Marriott downtown. Have dinner at the Golden Light Cantina.
Day 7
Amarillo to Tucumcari (115 Miles)
The next morning, have breakfast at the Stockyard Café and tour Amarillo’s historic district. Don’t miss Cadillac Ranch about 6 miles west as you leave Amarillo. Drive about 40 miles and stop at the MidPoint Café for a photo op, marking the halfway point on Route 66. Cross the state border in 22 miles as you enter New Mexico. Drive 40 miles to Tucumcari and tour the murals. Stay the night in the iconic Blue Swallow Motel.
Day 8
Tucumcari to Santa Fe (120 Miles)
The next day, eat breakfast at the Comet II Drive-In in Santa Rosa, which is about an hour away from Tucumcari. Take the pre-1937 alignment and drive 120 miles to Santa Fe. Tour the historic La Fonda, a former Harvey House and have lunch at Santa Fe Bite. After lunch, stroll the shops on The Plaza and step way back into the past at the Palace of the Governors, the oldest public building in the U.S. Have dinner at Tomasita’s and see a flamenco performance at El Farol’s and call it a night at Hotel Chimayo.
Day 9
Santa Fe to Taos (80 Miles)
Have breakfast at Tia Sophia’s and detour north on the High Road that winds through historic villages for 80 miles to Taos. On the way, have lunch at Sugar Nymphs Bistro, near Peñasco. Stop at the Rio Grand Gorge Bridge and then head to Earthship Biotecture to tour the world’s largest off-the-grid community. Eat dinner at La Cueva and stay in an Earthship overnight; if they’re full, spend the night at the El Pueblo Lodge in Taos.
Day 10
Taos to Albuquerque (150 Miles)
Drive 150 miles south to Albuquerque and have lunch at Duran Central Pharmacy. Tour Old Town, catch a movie at the historic KiMo Theatre and have dinner at the Standard Diner. Spend the night at the lovely Los Poblanos Inn or sleep in an Airstream trailer at Enchanted Trails RV Park.
Day 11
Albuquerque to Winslow (270 Miles)
This day, visit the Acoma Pueblo, about 70 miles west of Albuquerque. Stop in Gallup to shop the trading posts and see the historic El Rancho Hotel before crossing the border into Arizona. About 45 miles from the border, drive through the Painted Desert then stop for lunch in Holbrook at Joe & Aggie’s Café. Spend the evening at La Posada in Winslow, about 30 miles west. For an upscale experience, dine at the Turquoise Room; for something more casual, but just as delicious, eat at the E & O Kitchen.
Day 12
Winslow to Kingman (200 Miles)
Today, drive 60 miles toward Flagstaff. Tour the historic downtown, have breakfast at Miz Zips; if you’re looking for something different, Satchmos is a good choice. Drive 30 miles to Williams. Spend an hour roaming through downtown and then head to Seligman for lunch at Angel’s Delgadillo’s Snow Cap Drive-In. Chat with locals and tourists and then set out to take the pristine two-lane drive to Kingman, passing through Peach Springs and Hackberry. Spend the night in Kingman at the El Trovatore or for more modern accommodations try the Springhill Suites.
Day 13
Kingman to Barstow (210 Miles)
Leave Kingman driving the 1926 alignment via the Oatman Highway, a scenic winding road through the Black Mountains. But take your time—the road has hairpin turns, steep mountain grades, and 15-mph switchbacks. In Oatman, stop at the General Store, feed the town burros, and have lunch at the Oatman Hotel & Restaurant, where the walls are papered with more than 100,000 one-dollar bills. As you cross the border into California, gas up in Needles because you’ll soon be driving through the Mojave Desert. From Needles, it’s 140 miles west to Barstow. If you’re up for a very cool side trip, drive about 60 miles south to the town of Joshua Tree (passing the iconic Roy’s Motel in Amboy). Joshua Tree has beautiful accommodations, like Joshua Tree Mountain Vista.
Day 14
Barstow to Los Angeles (130 Miles)
In Joshua Tree, have breakfast at Crossroads Café and take a driving tour of Joshua Tree National Park before hitting the road for the final stretch to Los Angeles. From Barstow, it’s 75 miles to the Fair Oaks Pharmacy in Pasadena, a good place to have a vintage sweet treat or just browse the 1915 soda fountain.
Time your arrival into downtown LA before 3pm to avoid traffic. The original Route 66 terminus is at 7th and Broadway. This historic downtown area is undergoing a revitalization, so there’s a lot to see and do. Tour the galleries, grab a bite at the Grand Central Market, and stay at the Ace Hotel or Hotel Figueroa. If you head to Santa Monica and it’s a weekday, try not leave downtown after 2pm; the 15-mile drive to Santa Monica can take 1.5 hours during rush hour. In Santa Monica, meet the end of the Mother Road at the edge of the glorious Pacific Ocean at the Santa Monica Pier.
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