Route 66 - Westbound

Overview

This trip by season

The same trip. Very different weeks.

• Spring

  March to May

  Rivers running high

  Rivers full of snowmelt and the parks ahead of the summer rush. Some high roads and passes open later in the season.

  2 spring departures ›

• Summer

  June to August

  Everything open

  The full itinerary runs and every road and trail is open. These dates are popular, so they fill first.

  1 summer departure ›

Day by day

1. 

   

   

   

   

   

   Day 1

   Arrival and Explore Chicago, IL

   Arrive in the Windy City and transfer to your hotel in the heart of Chicago. Please arrive no later than 2 PM Central Standard Time. After some time to relax and freshen up, begin your Route 66 experience with a wonderful Architecture River Cruise of Chicago’s downtown area. Serene and bathed in a softer light with the shadows of the late afternoon sun, the cities architecture takes on a whole new life as it begins its transition from day to night.

   Then join the group for a Chicago-style deep-dish pizza dinner at a local restaurant. Finish your day with a short walk to the starting point of “The Mother Road.” There is no better place to start your Route 66 experience than at the Historic Route 66 Begin Sign where you are sure to want a few pictures.

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2. 

   

   

   Day 2

   Chicago, Pontiac, Springfield, IL

   After breakfast, depart Chicago with a scenic drive past the iconic Willis Tower before setting out on one of America’s most legendary highways—Historic Route 66, the “Mother Road.” Wherever possible, you’ll travel along original stretches of Old Route 66, immersing yourself in the nostalgia, roadside charm, and Americana that define this classic journey.

   Your Route 66 adventure begins with a stop at Ambler’s Texaco Station in Dwight, a beautifully preserved 1930s gas station that captures the spirit of early road travel. Continue to the Standard Oil Station in Odell, another restored landmark that offers a glimpse into the golden age of American motoring. In Pontiac, Illinois, enjoy a visit to the Route 66 Association of Illinois Hall of Fame & Museum, where vintage memorabilia, classic cars, and colorful murals celebrate the history and cultural impact of the Mother Road. Lunch is on your own in Pontiac, giving you time to explore the charming downtown.

   This afternoon, continue along Route 66 through Towanda, Normal, and Lincoln, discovering restored signage, classic roadside attractions, and small-town Americana along the way. By evening, arrive in Springfield, Illinois, the hometown of Abraham Lincoln. After checking into your hotel, gather with your group for a fun and nostalgic dinner at the legendary Cozy Dog Drive In—the official birthplace of the corn dog and a true Route 66 institution.

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3. 

   Day 3

   Springfield, IL to St Louis, MO

   Begin your day with a visit to the Abraham Lincoln Presidential Library & Museum which documents the life of the 16th U.S. President, Abraham Lincoln, and the course of the American Civil War. Also, there will be a stop at his home before leaving Springfield and traveling to St Louis, MO. Enroute to St Louis you will explore multiple locations along the original Route 66 routing including Auburn, Virden, Girard, and Litchfield. After a stop in Mt Olive, you will continue to Granite City before the historic Chain of Rocks Bridge in St Louis. Late this afternoon you will be able to enjoy a tour of Gateway Arch including a tram ride to the top. The evening will be yours to enjoy the downtown St Louis area including historic Union Station, the Ballpark, and the waterfront along the Mississippi River.

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4. 

   Day 4

   Meramec Caverns to Springfield, MO

   This morning you will continue west on the Old Road to an iconic stop, Meramec Caverns. Beneath the fertile rolling hills of the Meramec Valley, lies a complex of mineral formations and color as rare and unique as they are beautiful. Enjoy a guided tour of these beautiful caverns, then continue to Cuba with time to explore the 14 amazing murals. Explore more sights along the Route 66 corridor including the world-famous Route 66 Giant Rocking Chair, Giant Faucet and the Route 66 Motors & Gift Shop in Rolla. Arrive in Springfield, MO for overnight and dinner at Jimm’s Steakhouse.

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5. 

   Day 5

   Springfield, MO to Tulsa, OK

   After breakfast, depart Springfield with some famous Route 66 sites including Gary Gay Parita, Spencer, Avilla, Carthage and Joplin, MO. Once finished with Missouri you will travel Route 66 into Kansas with a picture stop at Cars on the Route in Galena and visit the famous Marsh Arch Bridge. Cross into Oklahoma and arrive in Miami for touring of the historic Coleman Theater. Enjoy stops at Ed Gallaway’s Totem Pole Park and the Blue Whale as you travel the Mother Road. Upon arrival in Tulsa, OK you will get to visit the various points/stops within the city. You will also visit the Cyrus Avery Plaza who is known as the Father of Route 66. Enjoy your evening exploring this historic town.

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6. 

   Day 6

   Tulsa to Oklahoma City

   Begin your day with a visit to the Route 66 Historical Village and a few other iconic Tulsa locations before moving on the Mother Road. Enjoy a journey along historic Route 66 including a stop in Sapulpa for a tour of their famous Gasoline Alley Classics and the Rock Café. A brief stop will be made in Davenport before arriving in Chandler for touring of the Route 66 Interpretive Center. The Center takes visitors on a visually entertaining “drive” from the 1920’s through current-day Oklahoma on what author John Steinbeck called, in his classic novel, The Grapes of Wrath, our “Mother Road,” Route 66. You will also visit McJerry’s Route 66 Gallery. This is home to an award-winning artist and Route 66 historian and writer. Continue with stops at Seaba Station Motorcycle Museum, a visit to the Arcadia Round Barn and a fun rest stop at POPS, an iconic stop along the Old Hwy. With over 600 different kinds of soda, a POPS soda guru can guide you to a refreshing alternative or an old time favorite.

   Arrive in Oklahoma City and finish your day at the First Americans Museum. Opened in 2021, visitors experience the collective histories of 39 distinctive First American Nations in Oklahoma today. First Americans Museum shares the cultural diversity, history, and contributions of the First Americans. These people are as much a part of Route 66 History as everything else we experience. Once finished you will travel to your hotel in the heart of Bricktown with the evening free to explore and have dinner on your own.

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7. 

   Day 7

   Oklahoma City to Amarillo

   This morning, enjoy a tour of the Oklahoma City National Memorial, which honors the victims, survivors, rescuers, and all who were affected by the Oklahoma City bombing on April 19, 1995. Depart Oklahoma City and continue your Route 66 journey westward, first stopping in Clinton for lunch on your own, followed by a tour of the Oklahoma Route 66 Museum. The museum offers visitors a personal journey through the history of the nation's most revered highway from a perspective of the state where it all began. Encounter the iconic ideas, images, and myths of the Mother Road. Learn about the dreams and the labor needed to make the road a reality. A bit further down the road in Elk City, explore various sites and unique locations in this rural town. Continue west to Amarillo, your destination for the day. After checking into your hotel, join the group for an authentic Texas experience at the Big Texan!

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8. 

   Day 8

   Amarillo to Albuquerque

   As you leave Amarillo this morning following the Mother Road west, a must stop is the Cadillac Ranch. Invented and built by a group of art-hippies imported from San Francisco. Ten Caddies were driven into one of Stanley Marsh's fields, then half-buried, nose-down, in the dirt (supposedly at the same angle as the Great Pyramid of Giza). They face west in a line, from the 1949 Club Sedan to the 1963 Sedan de Ville, their tail fins held high for all to see on the empty Texas panhandle. A must stop will be at Route 66 halfway point in Adrian, TX. Afterwards we will cross the border into “The Land of Enchantment,” New Mexico, and enjoy the Route 66 nostalgia of Tucumcari which is home to many iconic Route 66 sights such as the Blue Swallow Motel, Tee Pee Curios, La Cita Mexican Restaurant, and a shining monument to the Old Road. In Santa Rosa, drive Route 66 through town and stop at Joseph’s Bar & Grill for lunch.

   Enjoy more time following the old route as you make your way north on the original Route 66 route into Santa Fe. Explore downtown Santa Fe, NM before journeying down to Albuquerque. The rest of the day is free to explore historic Old Town Albuquerque on your own. Old Town’s narrow streets and century-old adobe houses are home to New Mexican eateries serving enchiladas and sopaipilla pastries, and tiny artisan shops selling jewelry, rugs, and pottery. Old Town Plaza is a charming spot overlooked by 18th-century San Felipe de Neri Church.

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9. 

   Day 9

   Albuquerque, NM to Flagstaff, AZ

   This morning, depart Albuquerque and travel west with a stop for lunch in Gallup at the El Rancho Hotel, a delightful old hotel lovingly preserved in its 1930's glory. Continue westward, entering Arizona and arrive at Petrified Forest National Park for an afternoon of sightseeing. After lunch, enjoy a scenic drive through the Painted Desert and on Blue Mesa with picture stops along the way. Then walk through the Crystal Forest before exiting the park. Next drive through another town full of Route 66 nostalgia and made famous in a song, Winslow, AZ. After a full day on Route 66, arrive in Flagstaff for a free evening exploring this amazing and eclectic downtown area.

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10. 

    Day 10

    Flagstaff, AZ to San Bernardino, CA

    A short drive west of Flagstaff lies the small town of Seligman, now known as “The Birthplace of Historic Route 66” and a must see for Route 66 fans. In 1972, Angel Delgadillo moved his barber shop so that he could take advantage of the traffic on the new alignment of Route 66 through Seligman. Business was good until September of 1978, when I-40 bypassed Seligman. To stimulate tourism, Angel, his wife Vilma, and other shop owners in northwest Arizona established the Historic Route 66 Association of Arizona. From here you will drive the longest remaining stretch of the original road through towns like Peach Springs and Hackberry on your way to Kingman with a stop at Mr. D’z Route 66 Diner for lunch on your own. After lunch, it is an interesting and scenic drive through the desert mountains as you make your way to the old mining ghost town of Oatman. Located at elevation 2,700 feet on old Route 66 between Kingman, Arizona, and Needles, California, the popular small town is an interesting stop, with numerous gift shops and small restaurants. From Oatman, pass through Needles and then arrive in Barstow for for dinner at a local restaurant, before heading to San Bernardino and staying overnight at the fun and historic Wigwam Motel

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11. 

    Day 11

    Hollywood-Santa Monica, CA

    Stop for breakfast at a local diner and then travel to Hollywood for a fun tour of Hollywood, West Hollywood and Beverly Hills. You will see The Hollywood Sign, The Walk of Fame, Dolby Theater, Laugh Factory, Sunset Strip, Rodeo Drive, Route 66, Capitol Records, Filming Locations, Chinese Theatre, and celebrity homes in Beverly Hills. After an exciting tour, stop at a local diner for lunch on own. In the afternoon, take a short drive to the Santa Monica Pier and visit the western terminus of America’s Main Street, Route 66. Enjoy free time to explore the pier on your own. Then celebrate this wonderful journey along the Mother Road as you join your fellow travelers for a farewell dinner on the pier. A fitting end to a nostalgic trip!

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12. 

    

    

    

    

    Day 12

    Travel Day

    Transfer to the Los Angeles Airport for your departure flight home.

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SWAT Trip Protection Plan

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