Route 66 - 3 Week Itinerary

Route 66 is more than just a road—it’s a legendary journey that captures the spirit of American freedom and adventure. Stretching from Chicago to Santa Monica, this iconic highway winds through eight states, revealing a kaleidoscope of landscapes, small towns, and roadside Americana along the way. Often called the “Main Street of America,” Route 66 is lined with vintage diners, neon-lit motels, and quirky attractions that embody the charm of a bygone era. Driving this historic route isn’t just about the destination—it’s about embracing the open road, savoring the unexpected, and experiencing a slice of true Americana. With every mile, Route 66 offers a timeless reminder of the joy of exploration and the enduring magic of the great American road trip.

Week 1: Illinois and Missouri

Day 1: Chicago, Illinois

Explore Chicago: Visit Millennium Park, Willis Tower, The Art Institute of Chicago, and the Route 66 Begin sign on Adams Street.

Overnight in Chicago.

Day 2: Chicago, IL to Springfield, IL (200 miles)

Stops: Visit Joliet (Old Joliet Prison, Rialto Square Theatre), Wilmington (Gemini Giant), Pontiac (Route 66 Hall of Fame and Museum).

Explore Springfield: Visit the Abraham Lincoln Presidential Library and Museum, Lincoln’s Home.

Overnight in Springfield.

Day 3: Springfield, IL to St. Louis, MO (100 miles)

Stops: Henry's Rabbit Ranch in Staunton, Chain of Rocks Bridge.

Explore St. Louis: Visit the Gateway Arch, and enjoy the city’s vibrant food scene.

Overnight in St. Louis.

Day 4: St. Louis, MO

Explore St. Louis: Tour the Missouri Botanical Garden, visit the City Museum, and explore Forest Park.

Overnight in St. Louis.

Day 5: St. Louis, MO to Rolla, MO (110 miles)

Stops: Route 66 State Park, Meramec Caverns, and Jesse James Wax Museum.

Overnight in Rolla.

Day 6: Rolla, MO to Springfield, MO (110 miles)

Stops: The Totem Pole Trading Post in Rolla, and visit Devil’s Elbow.

Explore Springfield: Visit the Route 66 Car Museum.

Overnight in Springfield, MO.

Day 7: Springfield, MO to Joplin, MO (75 miles)

Stops: Route 66 attractions in Carthage, including the 66 Drive-In Theatre.

Overnight in Joplin.

Week 2: Kansas, Oklahoma, and Texas

Day 8: Joplin, MO to Tulsa, OK (115 miles)

Stops: Galena (Cars on the Route), Baxter Springs, visit the Blue Whale of Catoosa.

Explore Tulsa: Visit the Philbrook Museum of Art, and the Woody Guthrie Center.

Overnight in Tulsa.

Day 9: Tulsa, OK

Explore Tulsa: Take a walking tour of the Art Deco architecture, and visit the Route 66 Historical Village.

Overnight in Tulsa.

Day 10: Tulsa, OK to Oklahoma City, OK (105 miles)

Stops: Sapulpa (Heart of Route 66 Auto Museum), Chandler (Route 66 Interpretive Center).

Explore Oklahoma City: Visit the Oklahoma City National Memorial and Museum.

Overnight in Oklahoma City.

Day 11: Oklahoma City, OK to Clinton, OK (85 miles)

Stops: El Reno (Fort Reno), Hydro (Lucille's Service Station).

Explore Clinton: Visit the Oklahoma Route 66 Museum.

Overnight in Clinton.

Day 12: Clinton, OK to Amarillo, TX (180 miles)

Stops: Elk City (National Route 66 Museum), Shamrock (U-Drop Inn), Groom (Leaning Tower of Texas).

Explore Amarillo: Visit Cadillac Ranch, and the Big Texan Steak Ranch.

Overnight in Amarillo.

Day 13: Amarillo, TX

Explore Amarillo: Visit Palo Duro Canyon State Park, the second-largest canyon in the U.S.

Overnight in Amarillo.

Day 14: Amarillo, TX to Tucumcari, NM (115 miles)

Stops: Vega (Magnolia Station), Adrian (Midpoint of Route 66).

Explore Tucumcari: See the Route 66 Monument, and visit the Tucumcari Historical Museum.

Overnight in Tucumcari.

Week 3: New Mexico, Arizona, and California

Day 15: Tucumcari, NM to Santa Fe, NM (165 miles)

Stops: Santa Rosa (Route 66 Auto Museum), Moriarty (El Comedor de Anayas).

Explore Santa Fe: Visit the Georgia O'Keeffe Museum, and walk around the historic Plaza.

Overnight in Santa Fe.

Day 16: Santa Fe, NM

Explore Santa Fe: Explore Canyon Road, the Loretto Chapel, and the New Mexico History Museum.

Overnight in Santa Fe.

Day 17: Santa Fe, NM to Gallup, NM (200 miles)

Stops: Albuquerque (Old Town, Route 66 Diner), Grants (El Malpais National Monument).

Explore Gallup: Visit the historic El Rancho Hotel.

Overnight in Gallup.

Day 18: Gallup, NM to Flagstaff, AZ (185 miles)

Stops: Petrified Forest National Park, Painted Desert, Winslow (Standin' on the Corner Park).

Explore Flagstaff: Visit the Lowell Observatory.

Overnight in Flagstaff.

Day 19: Flagstaff, AZ to Kingman, AZ (150 miles)

Stops: Meteor Crater, Walnut Canyon National Monument, Seligman (historic Route 66 town).

Explore Kingman: Visit the Historic Route 66 Museum.

Overnight in Kingman.

Day 20: Kingman, AZ to Barstow, CA (205 miles)

Stops: Oatman (wild west town with burros), the Mojave Desert, and Roy's Motel & Café in Amboy.

Explore Barstow: Visit the Route 66 Mother Road Museum.

Overnight in Barstow.

Day 21: Barstow, CA to Santa Monica, CA (130 miles)

Stops: Calico Ghost Town, Elmer's Bottle Tree Ranch in Oro Grande, and the Wigwam Motel in San Bernardino.

Arrive in Santa Monica: End your journey at the Route 66 End of the Trail sign on the Santa Monica Pier.

Overnight in Santa Monica.

Day 22: Santa Monica, CA

Relax in Santa Monica: Enjoy the beach, shop along Third Street Promenade, and explore the Getty Villa.

Overnight in Santa Monica.

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