Looking for a family-friendly excursion this fall? Embark on the great American road trip along Route 66. Romance for the open road and nostalgia for a simpler time characterize the historic route which spans over 2,000 miles and runs from Chicago all the way to Los Angeles. While the entirety of the route can be completed in two weeks, we recommend that you take your time and stop off in each city along the way to make the most of your road trip.
Chicago, Illinois to Springfield, Illinois
Depending on whether you are traveling East or West-bound, Chicago is either the official starting or ending point. Before you begin your trip, we recommend staying in Chicago a few days to soak up some history and culture. Looking for a place to stay in Chicago? Check out these great hotel deal.
When you are ready to hit the road, start at Jackson Boulevard at Lake Shore Drive which will take you out of Chicago. Once you get out of Chicago driving towards Pontiac, you will hit some Route 66 attractions such as the Muffler Men, the Route 66 Hall of Fame, Swinging Foot Bridges, restored old gas stations, and a maple syrup shop that dates back to 1824. History buffs will want to explore the many sites relating to Abraham Lincoln, including the town of Lincoln. End your day in Springfield with a stop at the famous Cozy Dog Drive-In and a movie at the Route 66 Drive-In.
Illinois to Missouri
Continue on to St. Louis, where you will pass through Staunton, home to the famous Henry’s Rabbit Ranch and Route 66 Emporium. From there, cross the Mississippi river at the Chain of Rocks Bridge. Don’t forget to snap a picture in front of the iconic Gateway Arch and grab a frozen dessert at Ted Drewes Frozen Custard Stand in St. Louis before hitting the road again.
Missouri to Oklahoma
From St. Louis continue on to the famous Meramec Caverns in Sullivan before stopping for dinner in Springfield for a burger at Red’s Giant Hamburg, thought to be the world’s first drive-through restaurant. Other must-sees for this leg of the trip include the colorful murals in Cuba, the Mule Trading Post in Rolla, the Trail of Tears, and the world’s largest rocking chair.
Oklahoma to Texas
On your way to Tulsa, you can't miss stopping at one of Route 66’s most iconic attractions, the Blue Whale of Catoosa. After taking a few pictures in front of the giant blue whale, eat lunch at Clanton’s Cafe, the oldest family-owned restaurant on Route 66. Be sure to admire the Art Deco architect in Tulsa before continuing onwards to Oklahoma City where cowboy fans will enjoy visiting the National Cowboy & Western Heritage Museum.
Arrive hungry to the city of El Reno, which boasts a number of classic Route 66 eateries. We recommend filling up on the fried onion burger at Robert’s Grill. This local delicacy was invented during the Great Depression in 1926.
Texas to New Mexico
Crossing over into Texas, stop in Shamrock to admire the Art Deco Tower Service Station and U-Drop Inn. Continue on to Amarillo and enjoy a meal at the Big Texan Steak Ranch restaurant before checking out the art installation of buried Cadillacs aptly named, Cadillac Ranch.
Tucumcari, New Mexico to Albuquerque, New Mexico
Make your way to Tucumcari, a city known for having over 2,000 motels. Some of the more famous ones include the Blue Swallow, Motel Safari, and Pow Wow Inn; all of which come complete with the iconic Route 66 neon signs. After a good night's sleep, continue driving through the heart of New Mexico where you have the option of taking a slower route that passes through Sante Fe or taking the main route that cuts across to Albuquerque. Whichever one you choose, we recommend stopping in Albuquerque as it has the longest stretch of Route 66 and boasts many iconic buildings, signs, and restaurants.
Albuquerque, New Mexico to Flagstaff, Arizona
From Albuquerque, make sure you stop to admire the view across the plains of Acoma Pueblo, home to the Acoma Pueblo tribe. From there continue on into Arizona. This stretch includes many high-interest attractions including the Painted Desert, Petrified Forest National Park, and of course the Grand Canyon. Stop in Holbrook where you can see the Wigwam Motel, one of two surviving concrete teepees, the Bucket of Blood Saloon, and the former Navajo County Courthouse. Continue on to Winslow for some iconic Route 66 restaurants, cafes and gas stations before heading to Flagstaff.
Flagstaff, Arizona to Kingman, Arizona
Once you reach Flagstaff, you will want to stop and visit Lowell Observatory. Other attractions include, the Pioneer Museum, Riordan Mansion State Historic Park, Coconino National Forest, and Sunset Crater Volcano National Museum. Flagstaff makes for a great jumping off point for anyone who wants to explore the Grand Canyon. From Flagstaff, continue on to Seligman and have a bite at the Snow Cap Drive-Inn before making your way to Kingman.
Arizona to California
From Kingman to Needles, California you will find the longest (intact) section of Route 66. This stretch will pass through old mining towns, turned ghost towns. Stop in the former mining town of Oatman where you can live out your Wild West dreams. Cross over into California and stay a night in Needles. From here, you can easily take some detours to explore the Mojave Desert, Joshua Tree, and Havasu Falls. Grab breakfast in Barstow before making your way to Los Angeles. End your epic road trip at Santa Monica pier and gaze out at the expansive Pacific Ocean.
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