Self-Guided 14-Day Route 66 Motorcycle Tour: Route, Planning, & More

Sep 8, 2025

If you've ever thought about traveling Route 66 by motorcycle, there's a reason so many riders keep coming back to it. This road was once the main route across the country, stretching from downtown Chicago all the way to the Pacific Ocean in Santa Monica. A Route 66 motorcycle trip takes you through places that still look and feel like the early days of cross-country travel, with old gas stations, neon-lit motels, and small towns that remember when this road was the busiest one around.

The route we’ve put together covers 14 days and follows the original path as closely as possible. You won’t need to rush each day, and there’s room to explore without getting too far off track. Below, we’ve laid out each day with suggested stops and highlights to help you plan your ride.

Interested in having someone lead the way? Riders Share also offers Route 66 USA motorcycle tours with local guides who know the road inside and out. It's another way to experience the route without missing the stops that make it special. Browse upcoming tours and book your spot directly through Riders Share.

RT 66 Motorcycle Trip 14-Day Itinerary

NOTE: Route 66 was decommissioned decades ago, so the original road now runs alongside highways and through small towns as business routes or frontage roads. We’ve built this around the historic path, using the sections of road that still match the original route.

• Day 1: Chicago, IL to Springfield, IL
• Day 2: Springfield, IL to St. Louis, MO
• Day 3: St. Louis, MO to Springfield, MO
• Day 4: Springfield, MO to Tulsa, OK
• Day 5: Tulsa, OK to Oklahoma City, OK
• Day 6: Oklahoma City, OK to Amarillo, TX
• Day 7: Amarillo, TX to Tucumcari, NM
• Day 8: Tucumcari, NM to Santa Fe, NM
• Day 9: Santa Fe, NM to Gallup, NM
• Day 10: Gallup, NM to Flagstaff, AZ
• Day 11: Flagstaff, AZ to Kingman, AZ
• Day 12: Kingman, AZ to Needles, CA
• Day 13: Needles, CA to Barstow, CA
• Day 14: Barstow, CA to Santa Monica, CA

Day 1: Chicago, IL to Springfield, IL

Your Route 66 ride kicks off at the official starting point in downtown Chicago, right at the historic ”Begin Route 66” sign near Adams Street and Michigan Avenue. From there, it’s about 200 miles south to Springfield, the state capital and your first overnight stop. The ride is completely manageable for day one and gets you out of city traffic fairly early on. As you head south, you’ll pass through classic Illinois Route 66 towns like Joliet, Pontiac, and Lincoln, each one full of photo ops, vintage signs, and small-town diners that still carry the spirit of the Mother Road. This stretch lays the groundwork for everything ahead, giving you an early taste of the rhythm Route 66 is known for.

Need a bike to start off your trip? Riders Share has motorcycle rentals available right in Chicago. Browse the options and book your rental before day one.

Day 2: Springfield, IL to St. Louis, MO

The next stretch runs about 98 miles, making it much shorter than the day before and giving you time to enjoy the ride at a slower pace. From Springfield, the route passes through spots like Litchfield, where the Ariston Café has been serving Route 66 travelers since 1924. You'll start to feel the shift from quiet backroads to city surroundings as you roll into St. Louis. Riding over the historic Chain of Rocks Bridge brings you into town with a clear view of the Gateway Arch ahead, marking the end of your second day on the road.

Day 3: St. Louis, MO to Springfield, MO

Leaving St. Louis, the ride to Springfield, Missouri covers about 216 miles and brings you through some of the most well-preserved parts of the route so far. In Cuba, the buildings are covered in hand-painted murals that reflect the town’s past, and as you continue through Rolla, you’ll notice stretches of the original road still cutting through town like it hasn’t moved in decades. A little farther down, the Munger Moss Motel in Lebanon still glows with its vintage neon sign, a piece of roadside history that’s been around since the 1940s. Springfield, where you’ll end the day, holds a special place in Route 66 history since it’s the city where the name was first proposed back in 1926, which gives the place a bit of extra weight for riders tracing the full path.

NOTE: The Munger Moss Motel is permanently closed, but if you’re looking for something with that same Route 66 vibe, the Rail Haven Hotel in Springfield keeps things in theme and still feels connected to the road.

Day 4: Springfield, MO to Tulsa, OK

The route from Springfield to Tulsa is just under 190 miles and brings you through the last stretch of Missouri before cutting across a small section of southeastern Kansas. Galena has a restored Kan-O-Tex gas station with an old tow truck out front that inspired the character “Mater” from the Cars movie, and Baxter Springs still has original buildings from the Route 66 era. After crossing into Oklahoma, the road leads through places like Commerce and Claremore before reaching Tulsa, where parts of the old route still run straight through the heart of the city.

Day 5: Tulsa, OK to Oklahoma City, OK

There are about 108 miles between Tulsa and Oklahoma City, and most of it stays true to the original Route 66 alignment. Sapulpa and Stroud both have stretches of the old road still in use, and Arcadia is home to two of the most recognizable stops on this part of the trip. The Round Barn, built in the late 1800s, has been carefully restored and still stands right along the route. Just down the road, POPS is hard to miss with its glass walls lined with soda bottles and the giant bottle sculpture out front.

Day 6: Oklahoma City, OK to Amarillo, TX

This part of the route stretches around 260 miles and takes you across western Oklahoma into the Texas Panhandle. Clinton is home to the Oklahoma Route 66 Museum, and farther west, Elk City has another museum focused on roadside life along the Mother Road. As you cross into Texas, Shamrock stands out with its art deco Conoco Tower Station, one of the most photographed buildings on Route 66. Amarillo has its own share of landmarks, including the famous Big Texan Steak Ranch and the Cadillac Ranch installation just west of town.

Day 7: Amarillo, TX to Tucumcari, NM

Just before leaving Texas, Adrian marks the exact midpoint of Route 66, where a small café and weathered sign remind you that you’re halfway between Chicago and Santa Monica. Not far from there, Glenrio sits right on the state line, completely quiet now, with empty buildings that haven’t changed much since the highway moved on. 

The time zone shifts as you enter New Mexico, gaining an hour as the landscape starts to stretch wider and the road feels a little emptier. Tucumcari comes into view with rows of retro motels and bright neon signs, and spots like the Blue Swallow (book a night here to keep the Route 66 experience going!) and Tee Pee Curios still look just like the postcards that once advertised them.

Day 8: Tucumcari, NM to Santa Fe, NM

This stretch is about 170 miles if you follow the older alignment that loops north through Santa Rosa. Santa Rosa has a Route 66 Auto Museum filled with vintage cars, signs, and memorabilia that reflect the golden era of American road trips. From there, the original Route 66 veers off the main interstate and heads toward Santa Fe, offering a more scenic and historic option compared to the later Albuquerque bypass.

Day 9: Santa Fe, NM to Gallup, NM

Between Santa Fe and Gallup, the route connects with Albuquerque, where Central Avenue follows the original Route 66 path through the city. Nob Hill and downtown still feature neon-lit storefronts and retro diners. On the way to Gallup, the road passes through places like Grants and Laguna Pueblo, and you’ll start to notice more desert scenery and sandstone bluffs that define this part of the Southwest.

Day 10: Gallup, NM to Flagstaff, AZ

Crossing into Arizona, this leg runs about 185 miles and brings you through Holbrook, home of the Wigwam Motel with its teepee-shaped rooms, and Winslow, where the “Standin’ on the Corner” park draws in travelers from all over. Petrified Forest National Park sits right off the route, and it's one of the only national parks to include a stretch of Route 66 within its boundaries. Flagstaff, your stop for the night, has a strong Route 66 presence with vintage motels and shops still lining the road.

Day 11: Flagstaff, AZ to Kingman, AZ

This section holds some of the most iconic Route 66 scenery in the entire ride. Small towns like Williams and Seligman have leaned into their Route 66 roots, offering diners, shops, and museums that celebrate the history of the road. Angel Delgadillo’s barbershop in Seligman helped spark the revival of Route 66 tourism and is still a popular stop. The road into Kingman follows the old highway closely and passes through wide desert landscapes with little traffic and long views.

Day 12: Kingman, AZ to Needles, CA

After leaving Kingman, the route climbs into the Black Mountains and takes you through Oatman, a former mining town where wild burros still wander through the center of town. The road through Sitgreaves Pass is narrow with a few sharp turns, but the views make it worth the slower pace. Once you're past the mountains, the landscape opens up into the Mojave Desert as you head toward Needles, one of the most isolated towns along Route 66.

NOTE: This is the shortest day on the route, at just 63 miles between locations, which gives you time to slow down and explore a little more. Oatman is worth walking through, and if you're up for a detour, the old Route 66 alignment near Topock or the Mohave Museum of History and Arts back in Kingman are both good stops to stretch out the day.

Day 13: Needles, CA to Barstow, CA

This part of the trip runs deep through the desert, covering around 144 miles between Needles and Barstow. Along the way, you’ll pass Roy’s Motel and Café in Amboy, one of the most recognizable roadside stops in the Mojave. The landscape feels stripped down and wide open, and the route itself hugs parts of the old road that were once the main path across California’s inland desert.

Day 14: Barstow, CA to Santa Monica, CA

The final stretch brings you out of the desert and into the Los Angeles area as Route 66 makes its way toward the Pacific. Towns like Victorville and Pasadena still have original buildings from the highway’s earlier days, and parts of the old route wind through neighborhoods and business districts. The ride ends at the Santa Monica Pier, where the Route 66 “End of the Trail” sign marks the official finish of the road.

Explore Guided Route 66 Motorcycle Tours on Riders Share

While the itinerary above gives you everything you need for a self-guided trip, some riders prefer having a host lead the way. Riders Share offers guided motorcycle trips where each RT 66 motorcycle tour is shaped by the host, giving you a different take on the same legendary route. Some tours highlight the more iconic roadside landmarks, while others focus on lesser-known stretches that still hold on to that old Route 66 feel. You can browse current tours, compare different approaches, and book the one that fits your riding style.

Route 66 Motorcycle Trip Planning Tips

You don’t need to overplan every detail, but a few smart moves early on can make the whole ride smoother. Here are a few things worth thinking through before the trip starts:

• Use printed maps along with your phone. Route 66 signs can be inconsistent, especially in small towns or rural stretches. Some sections are marked clearly, others aren’t marked at all. Have a physical Route 66 map or a pre-downloaded GPS track saved just in case cell service drops or the signage disappears.
• Plan fuel stops in advance, especially in the Southwest. From Oklahoma westward, there are stretches where gas stations are spaced far apart. Don’t wait until your fuel light comes on to start looking. Fill up when you can, even if you’re only down half a tank.
• Book lodging early for popular spots. Towns like Tucumcari, Williams, and Santa Monica still have some of the original Route 66 motels, and many riders aim to stay in those places for the full experience. Some fill up fast during peak months or when large tours are running. It’s worth booking those in advance so you’re not stuck settling later.
• Expect short detours and realignments. Route 66 hasn’t been a federal highway since the 1980s, and some parts have shifted onto frontage roads, state highways, or business routes. A few segments are still under repair or fully bypassed. Nothing major, but don’t be surprised if the route jumps around a bit as you go.
• Don't treat this like a race. Some days might only cover 100 miles, and that’s on purpose. You’ll want time to stop, take photos, grab food, and talk to the people keeping this route alive. The pace is part of the experience, and rushing through it misses the point.

Make Route 66 Your Next Big Ride

There aren’t many rides that carry the same history and character as Route 66. From Chicago to Santa Monica, every stop adds another piece to the story of this road. A Route 66 motorcycle tour gives you the chance to see it all at a pace that lets the experience sink in. Start planning now and make this classic ride your next big trip!