Moon Route 66 Road Trip


By Jessica Dunham

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Moon Route 66 Road Trip reveals the ins and outs of this iconic highway, from sweeping prairies and retro roadside pit-stops to the stunning vistas of the Southwest. Inside you'll find:
  • Maps and Driving Tools: 38 easy-to-use maps detail the existing roads that comprise the original Route 66, along with site-to-site mileage, driving times, detailed directions for the entire route, and full-color photos throughout
  • Eat, Sleep, Stop and Explore: With lists of the best hikes, bites, roadside curiosities, and more, you can admire extraordinary landscapes like Acoma Pueblo or Joshua Tree National Park, explore big cities like Los Angeles and Chicago, or wander abandoned ghost towns. Immerse yourself in classic Americana with outsider art and kitsch masterpieces, find the most Instagram-worthy retro motels, and sample the breadth of regional cuisine, from deep dish pizza to carne asada
  • Flexible Itineraries: Moon Route 66 Road Trip covers Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California. Drive the entire original Mother Road in two weeks, or follow strategic routes for shorter trips to Chicago, Los Angeles, St. Louis, Santa Fe, and the Grand Canyon, plus side trips to Taos, Las Vegas, Joshua Tree, and Santa Monica
  • Expert Perspective: Jessica Dunham has driven thousands of miles along the famed highway and provides cultural insight, insider tips, and critical history of the route
  • Planning Your Trip: Know when and where to get gas and how to avoid traffic, plus tips for driving in different road and weather conditions and suggestions for international visitors, LGBTQ travelers, seniors, road-trippers with kids, and accessibility
With Moon Route 66 Road Trip's practical tips, detailed itineraries, and tried-and-true expertise, you're ready to fill up the tank and hit the road.

About Moon Travel Guides: Moon was founded in 1973 to empower independent, active, and conscious travel. We prioritize local businesses, outdoor recreation, and traveling strategically and sustainably. Moon Travel Guides are written by local, expert authors with great stories to tell—and they can't wait to share their favorite places with you.

For more inspiration, follow @moonguides on social media.




Driving Tips


14 Days on Route 66

Women of the Mother Road

Neon Photo Ops

Classic 66 Landmarks

Car Culture

Road trips are both blessed and burdened by the mythology of the open road. We have high expectations when we pack up the car and hit the pavement. We want to see places that charm, attractions that inspire, oddities that surprise. But more than that, we want to be transformed by the freedom that comes when we feel in charge of our own destiny.

There’s a reason that Route 66—a beating heart of blacktop running 2,448 miles (3,939 km) from Chicago to Santa Monica—lands on bucket lists of people from around the world. It’s the only journey that lives up to our grandiose vision of a road trip. That’s because its spirit was paved by pioneers, risk-takers, disruptors, poets, rule-breakers, and adventurers.

There’s Joy Nevin, a woman who trained as a pilot during World War II before traveling Route 66 as a saleswoman in a truck she retrofitted herself. There’s Victor Green, who created the Negro Motorist Green Book, a travel guide to help black motorists navigate Route 66 safely during the Jim Crow era. There’s writer John Steinbeck, whose novel The Grapes of Wrath encapsulated the desperate hope of emigrants who fled west during the Dust Bowl.

From Route 66’s birth in 1926 to now, the decades have carved out an identity for the road that shifts depending on where you are. Cosmopolitan cities like Chicago and Los Angeles stand in stark contrast to the laid-back pace of small towns like Seligman, Arizona. A shifting landscape changes with every mile, from rolling prairies to remote deserts to the crashing ocean. And abandoned ghost towns, like Glenrio, Texas, sit as reminders of all that is unknowable about the past.

To travel all of Route 66 requires endurance and grasping its long history necessitates perspective. Meeting the route’s residents calls for compassion and slowing down to see each and every sight demands patience. If you don’t possess those qualities when you begin your drive, you will by the end. A trip on Route 66 will transform you. The mythology is real.


Where to Go

Route 66 crosses eight states and three time zones. Some of the best-preserved sections of the road include the stretch between Springfield, Missouri, and Tulsa, Oklahoma; the road west of Seligman, Arizona; and the Oatman Highway through the Black Hills of Arizona.


Chicago: It’s here in America’s third-largest city that the Mother Road begins. It snakes southwest through Illinois and into St. Louis, Missouri. Though much of the route has been replaced by I-55, there’s still plenty of two-lane blacktop to explore. From Chicago, Route 66 heads to Pontiac. Make your first stop the Illinois Route 66 Hall of Fame & Museum, one of the best Route 66 museums on the journey. In Atlanta, eat like a local at the Palms Grill Cafe. You’ll learn about the 1908 Race Riots in Springfield, and in Staunton, stop to pet the furry, cuddly bunnies at Henry’s Rabbit Ranch.

Missouri and Kansas

Route 66 through Missouri gives you your first glimpse of Ozark country—tree-covered hills that gently rise and dip, and lush valleys that spread before you. This leg of the trip starts in St. Louis, where you’ll stroll the unusual Chain of Rocks Bridge, get interactive at the fun-for-everyone City Museum, and taste a custard “concrete” at Ted Drewes Frozen Custard. Take a break from the car with a walk around Laumeier Sculpture Park, in Kirkwood, visit landmarks from the Trail of Tears in Waynesville, and spend a day in Springfield, the official birthplace of Route 66.

The Mother Road only covers 13 miles (20.9 km) through Kansas, but you should still make time to visit Cars on the Route in Galena and stop for sandwiches at Nelson’s Old Riverton Store in Riverton.


Oklahoma has more drivable miles of Route 66 than any other state. You’ll cross early roadbeds and one of the longest bridges on the Mother Road, plus you’ll learn about some of the most significant racial events to shape our country’s history. In Catoosa, you can check out an oddball roadside attraction, the Blue Whale. Spend a few hours in Tulsa soaking up the art deco architecture before paying a visit to the Greenwood Cultural Center, which details the Tulsa Race Riot. In Arcadia, you can browse the selection of 600 sodas at Pop’s.


Route 66 runs directly west across the Texas Panhandle, parallel to I-40. The drive is peaceful and solitary, punctuated by rusting grain silos that jut out of the horizon and tiny towns set in the middle of nowhere. Don’t miss the art deco marvel, Tower Station and U-Drop Inn Café in Shamrock. In Groom, get pictures of the Leaning Water Tower before continuing west to Amarillo, where the famed Cadillac Ranch shows off 10 vintage Caddies buried nose-deep in a wheat field. A slice of pie at the MidPoint Café in Adrian marks the halfway point of this road trip and is a must-do.

New Mexico

From Texas, Route 66 crosses into the otherworldly landscape of red rocks and eternal sunsets that is New Mexico. Tucumcari, a former outlaw town, boasts plenty of retro neon signage, while artsy Santa Fe beckons travelers to browse the galleries and stay for a traditional New Mexican meal. The route dips south to Albuquerque before winding past Acoma Pueblo, which offers a fascinating look at American Indian history and culture. In Gallup, you’ll meet the nicest townsfolk ever as you traverse the sidewalks on the Mural Walking Tour.

Santa Fe, New Mexico

Tower Station and U Drop Inn Café in Shamrock, Texas

Chicago, Illinois.


I-40 is the present-day Route 66 in eastern Arizona. It takes you along the high desert and through quirky Southwest towns such as Holbrook (have lunch at Joe & Aggie’s Café) and Winslow (overnight at La Posada Hotel & Gardens) before heading into the pine trees of mountainous Flagstaff and Williams. After reaching the iconic Delgadillo’s Snow Cap Drive-In in Seligman, Route 66 opens up to miles of untouched road all the way to Kingman. Brave the hairpin curves through the Black Mountains on the way to the mining town of Oatman.


The California stretch of Route 66 is marked by the stark beauty of the desert (Joshua Tree and the Mojave) and the glitz and glitter of Los Angeles before it concludes at the Santa Monica Pier. Stop in Oro Grande to explore the “forest” at Elmer Long’s Bottle Tree Ranch and indulge in the big portions at Emma Jean’s Holland Burger in Victorville. Pay a visit to Fair Oaks Pharmacy, a 1915 soda fountain in Pasadena. And then head west to the Pacific Ocean to mark your journey’s end.

a sign marking the end of Route 66 in Santa Monica

When to Go

The best time for a Route 66 road trip is from late spring to early summer and in the early fall. The weather is usually temperate and roads are open, as are most Route 66 businesses. Be cautioned, though; Flagstaff, Arizona, sits at an elevation of 7,000 feet (2,134 m), which means the first snowfall can arrive as early as October.

Avoid travel during August, when the temperatures can reach 110°F (43°C) or hotter in Texas, Arizona, New Mexico, and the California desert. Though it’s a dry heat in the Southwest, the states of Illinois, Missouri, Kansas, and Oklahoma can be oppressively muggy.

July through early September is the monsoon season in New Mexico, Arizona, and California. Heavy rainstorms and heat lightning can occur suddenly—almost every afternoon—and often with freak weather conditions such as hail, high winds, and poor visibility. The storms are spectacular but flash flooding can be deadly, and many roads, especially those in the California desert, become flooded and impassible.

Winter should be avoided altogether. This Route 66 road trip starts in Chicago, which is notorious for cold and brutal winters. Even the western leg of Route 66 is subject to inclement weather. From November to March, mountain passes through New Mexico and Arizona (near Flagstaff) may be closed due to snow and ice. Many Route 66 businesses close for the season from October to April.

Driving Tips

When Route 66 began in 1926, it was one of the few highways that cut 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 realignments were major, such as in New Mexico where the road changed direction, while others shifted the asphalt less than one-eighth of a mile (0.2 km).

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 of 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.


14 Days on Route 66

This two-week itinerary follows the route from Chicago to Santa Monica and includes major highlights as well as hidden gems and the best local eateries. Route 66’s diagonal route is unique when compared to the more common north-south or east-west trajectories of most major freeways. Its path cuts a swath through the heart of America. Plan to explore leisurely and meet the locals—a lot of the people who live and work on Route 66 run family-owned businesses that have been in operation for decades. Much of the route was realigned along the interstate highways, so if you need to make up time, you can jump on and off the freeway to reach your next destination quickly. Get ready for an up-close view of many of the cultures, dialects, and traditions that comprise America, from past to present.

Day 1: Chicago

Day one starts in Chicago (see details and suggestions on click here). Have lunch at The Green Door Tavern, then head to Pontiac to see the Illinois Route 66 Hall of Fame & Museum and walk across the swinging footbridges, the oldest of which is from 1898. Enjoy dinner at the Old Log Cabin Inn & Restaurant and spend the night at Three Roses Bed & Breakfast in Pontiac.

Day 2: Illinois
PONTIAC TO ST. LOUIS: 200-225 MILES (320-360 KM)

Start the day early and drive southwest about 50 miles (81 km) along Route 66 to Funk’s Grove to pick up some “sirup.” Have lunch at Ariston Café in Litchfield about 1.5 hours away (102 mi/164 km). Head to Staunton, about 15 miles (24 km) away, to say hello to the lovable rabbits at Henry’s Rabbit Ranch. In another 20 miles (32 km), you’ll get to Edwardsville, where you should have dinner at Cleveland-Heath. From there it’s only 23 miles (37 km) to St. Louis. Check into the Magnolia Hotel for the night.

Days 3-4: Missouri

Savor a hearty lunch at Fitz’s in St. Louis. Spend a few hours exploring Union Station or playing at the interactive City Museum. In the afternoon, drive about 80 miles (129 km) to Cuba to see the murals and the Wagon Wheel Motel. Stop in Fanning to get a picture of the World’s Largest Rocking Chair on Route 66. Head to Springfield, the birthplace of Route 66, and spend the night at the Best Western Route 66 Rail Haven.


Start the day with locally sourced eats at The Order before driving about 75 miles (121 km) to the Missouri state line at Joplin. Continue for a 13-mile (20.9-km) jaunt through Kansas, checking out Cars on the Route in Galena and ordering sandwiches to go at Nelson’s Old Riverton Store in Riverton. From there, cross into Oklahoma and plan to drive one of the oldest roadbeds on the journey: the Sidewalk Highway, between Miami and Afton. This 3-mile (4.8-km), 9-foot-wide (2.7-meter) stretch pre-dates Route 66 by about 15 years. From Afton, it’s 40 miles (64 km) to see the Andy Payne monument in Foyil and then another 30 miles (48 km) to Tulsa, where you’ll spend the night at The Mayo Hotel or Campbell Hotel.

Union Station in St. Louis, Missouri

the MidPoint Café in Adrian, Texas

Cadillac Ranch in Amarillo, Texas.

Day 5: Oklahoma

Have breakfast at Corner Cafe, before visiting the Greenwood Cultural Center, where you’ll learn about one of the worst race riots in U.S. history. Afterward, head west for 106 miles (171 km) to Arcadia and stop at Pops, a futuristic gas station and soda pop heaven. In Oklahoma City, check out the Gold Dome Building and Milk Bottle Grocery before tucking in for the night at Skirvin Hilton Hotel. Start your day with coffee and cake doughnuts at Brown’s Bakery, then check out the 1925 Lake Overholser Bridge at Route 66 Park.

Day 6: Oklahoma and Texas

Get on the road early to see the Pony Bridge in Geary, then drive about 115 miles (185 km) to the Texas state line. The beautifully restored Tower Station and U-Drop Inn Café in Shamrock should be your first stop. Drive about 20 miles (32 km) to McLean to tour the Devil’s Rope Museum. Grab lunch at the Red River Steakhouse. Head 70 miles (113 km) to Amarillo and stay overnight at the Courtyard by Marriott Amarillo Downtown. Dinner is right across the street at Crush Wine Bar.

Day 7: Texas

The next morning, tour Amarillo’s historic district. Don’t miss Cadillac Ranch, about 10 miles (16.1 km) west as you leave Amarillo. Drive about 40 miles (64 km), then stop for lunch, a slice of pie, and a photo op at MidPoint Café in Adrian—this marks the halfway point of your Route 66 road trip. Cross the state border in 22 miles (35 km) as you enter New Mexico. Drive 40 miles (64 km) to Tucumcari and tour the murals. Overnight at the iconic Blue Swallow Motel.

Days 8-10: New Mexico

Start the day with breakfast at Comet II Drive-In in Santa Rosa, which is about an hour from Tucumcari. Take the pre-1937 alignment for the beautiful 120-mile (193-km) drive to Santa Fe. See the impressive art collection at the Georgia O’Keeffe Museum, then enjoy a red chile enchilada at The Shed. After lunch, stroll the shops on The Plaza and tour The Palace of the Governors, the oldest public building in the United States. Toast a pre-dinner cocktail on the rooftop of the historic La Fonda (a former Harvey House), then dine at Tomasita’s. Before calling it a night at El Rey Court, see a flamenco performance at El Farol.


Breakfast should be at The Pantry before you detour north on the High Road for 80 miles (129 km) to Taos. On the way, have a light 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 fully booked, spend the night at the El Pueblo Lodge in Taos.


Drive 150 miles (242 km) south to Albuquerque and have lunch at Loyola’s Family Restaurant. 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.


On Sale
Oct 19, 2021
Page Count
376 pages
Moon Travel

author Jessica dunham

Jessica Dunham

About the Author

Jessica Dunham lives in Phoenix with her husband and two spunky dogs, but inherited a family summer home on Lake Champlain in Vermont. This seemed heavenly to her, until she tried to imagine getting there from halfway across the country. Then it required some effort and a little imagination. The only way to transport the herd from one place to another was to pile into a Jeep and drive. That's is how she came to know and love the Mother Road, and became an expert on the ins and outs of Route 66. 

She's since driven from Phoenix to Vermont and back again six times, traversed the Southwest portion of Route 66 hundreds of times, napped in leafy parks, slept in a wigwam and at a Best Western, camped in tents, dined at mom-and-pop eateries, met strangers, and made friends in almost every town dotting the famed highway. She's seen the sun rise over Illinois cornfields and watched it set over the Pacific Ocean. After all this, she considers the beating heart of blacktop from Chicago to Santa Monica home.

Formerly a travel guide editor at Madden Media, Jessica is now a freelance travel writer. Her writing has been featured in PHOENIX magazine, Valley Guide, Phoenix Travel Guide, Arizona Visitor's Guide, Midwest Living, Phoenix New Times, Modern Luxury, Annapolis Visitors Guide, Connecticut Visitors Guide, Runner's World, Jane, Discover South Carolina, and more. Jessica is also the author of The Open Road: 50 Best Road Trips in the USA.

Learn more about this author