Route 66

Use this Route 66 itinerary to plan your travels from Chicago to Santa Monica.  Historic Route 66 spans over 2,400 miles and crosses 8 states, starting in Chicago, Illinois and terminating at the Pacific Coast in Santa Monica, California. Given its “66” designation in 1926, it became a well-traveled highway, bringing together people from all walks of life.

Starting in Chicago.  

The beginning point of Route 66 in Chicago has changed over the years, originally starting on Jackson Boulevard at Michigan Avenue in 1926. Since 1933 the starting point has been Jackson Boulevard at Lake Shore Drive.  While in Chicago, many visitors seek out Grant Park, the Willis Tower, the museums, and the lakeshore shopping areas.

St. Louis

St. Louis is the largest city along Route 66 between Chicago and Los Angeles, and there are some sites related to the Mother Road within the region. Some of the streets have new names, but all of these locations are part of the Route 66 journey. Get your kicks at locations along the famed Mother Road in St. Louis.

Springfield, MO

Springfield’s emergence as the Birthplace of Route 66 began in the 1920s when the federal government first mandated the construction of a national highway system. A placard on the east side of Park Central Square commemorates Springfield’s subsequent 1992 designation as the official birthplace of Route 66.

One of the last remaining original stretches of Route 66 is at Glenstone Avenue and Kearney Street. Now the site of a Route 66-themed Kum & Go Fresh Market, the paved road is still accessible to motorists.

Joplin, MO

Joplin has several classic Route 66 attractions including two motels, and ten vintage service stations, plus diners, burger drive-ins, historic landmarks, and even Bonnie and Clyde’s hideout. 

Oklahoma City, OK

Get your kicks on more than 400 miles of Route 66 in Oklahoma. The nation’s longest driveable stretch of Route 66 cuts through Oklahoma, making its way past charming towns, roadside diners and quirky attractions. Experience Oklahoma City, Tulsa and authentic hometowns along the Mother Road where you’ll meet friendly people and find unique shopping and dining opportunities

Amarillo, TX

The Route 66 Historic District visitors will find over one mile of art galleries, antique and collectible stores, restaurants, and bars in historic buildings. Not only was Route 66 the Mother Road of America, but this district was one of the first residential and business districts in Amarillo. This historic strip is located on Sixth Ave. between Georgia & Western Streets in Amarillo, TX

Santa Fe, NM

Today, cautious motorists – whether driving 4×4 vehicles or not – renounce to follow certain Route 66 sections, especially under heavy rains (e.g., from Texas, entering New Mexico through Glenrio, it is highly advisable to back up and head over to Interstate I-40).

Gallup, NM

Gallup is where the Southwests and its Native American culture meets Route 66. Things to do: visit the Red Rock Park, venue for rodeos, bull-riding, the Inter-Tribal Indian Ceremonial and the Red Rock Balloon Rally. See the Classic Route 66 El Rancho Hotel, Armco Gas Station and the Denny’s Diner; the 1928 El Morro Theatre and the Lariat Lodge. Take a day tour to Visit Zuni Pueblo and Grants via El Morro National Monument and the “Badlands”

Grand Canyon, AZ

The magical Grand Canyon National Park is just north of Route 66 and is worth the slight detour. This 200-mile-long, dramatic canyon of the Colorado River is a destination in and of itself, and is easily one of the best natural formations along the historic route.

Santa Monica, CA

Santa Monica became a permanent part of the road’s history on January 1, 1936. As the city of Los Angeles grew, the original terminus was extended from downtown L.A. to the corner of Lincoln and Olympic Blvds. in Santa Monica. Confusion reigned over Route 66’s endpoint afterward, but the belief it ends at the Santa Monica Pier has always been incorrect. Federal Highway rules stated one highway must feed into another to not “dead-end” a traveler, so Route 66’s new ending was re-routed to connect with “Alt 101,” today’s California Pacific Coast Highway.

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