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Route 66, The Main Street of America – Part I


A journey down Route 66 is like cutting yourself a slice of All-American Pie. You’ll discover people and places you didn’t know existed – like the murals that line the walls of Pontiac, IL and Cuba, MO; Ted Drewes Frozen Custard in St. Louis and the magnificent Lincoln Presidential Library & Museum in Springfield, IL. Meet published Route 66 authors and experts, roadies and characters. If you love “off-the-beaten-track,” you’ve found your trip, a wonderful combination of history, Americana, and more great road food than you can imagine.


  • Classic/Roadie Accommodations - The Palmer House in Chicago, the Lincoln Hotel in Springfield, IL (2 nights), St. Louis (2 nights), Rail Haven, Springfield (MO), Miami (pronounced My-AM-ah), OK; the historic Mayon Hotel in Tulsa, Oklahoma City
  • Meet the people of Route 66 - special guides, speakers and guests; lots of quirky attractions
  • 23 meals, many of them in classic restaurants - everything from roadside diners to fancy sit-downs in historic eateries
  • Roundtrip airfare to Chicago/from OK City
  • Door-to-door airport transportation
  • 4400/5050 Gold Passport Points



Daily Itinerary

ChicagoDay 1

Day 1.

Fly to Chicago: Depart from Sacramento at 7am, arriving in Chicago in early afternoon.  Your first "roadie" experience is a stop for a meal at Del Rhea's Chicken Basket (1946).  Get a picture of the beginning of the Mother Road downtown at the Palmer House Hotel, a Chicago landmark. Palmer House Hotel (L)

Roadside AttractionDay 2

Day 2.

Chicago to Springfield: Our adventure begins in earnest with breakfast  at a Chicago landmark: Lou Mitchell's funky breakfast counter, celebrating their 100th year! Outside of Chicago we get off the interstate and follow the old road, joined by Route 66 author John Weiss.

Wind through Joliet (your first old highway museum) to the small community of Odell (where we photograph a beautifully restored old service station), on to Dwight for lunch.  View the memorabilia in the Route 66 Museum and the "walldogs" murals in Pontiac.  John has made restoring Route 66 sites his life's work.  Today he will show us an old jail, a giant robot, and other unique attractions.  Lincoln Hotel by Doubletree Springfield - 2 nights (FB, L)

SpringfieldDay 3

Day 3.

Springfield/Lincoln: Visit the critically-acclaimed Lincoln Presidential Library & Museum, before a lunch break at the famous Cozy Dog, where it is said the corn dog was invented.  An afternoon journey on Route 66 takes us to Lincoln, the only city named for the future president before he held office.  Learn the story.  Stop in Broadwell to salute a 66 legend, the late Ernie Edwards of the Pig Hip Restaurant.  There was the night Ernie met Harlan would know him as Colonel Sanders. (FB, L, D)

Cozy DogDay 4

Day 4.

Springfield to St. Louis: Our rural travels roll on through southern Illinois.  We stop to spruce up Our Lady of the Highways statue, another Route 66 landmark.  Stop in at the Rabbit Ranch and get a postcard autographed by...a rabbit of course.  Hear the story of Mother Jones, and get a picture of the Cannonball Jail and Million Dollar Courthouse in Carlinville.  An afternoon stop in St. Louis gives you a chance to discover the Gateway Arch and get views of the old highway from above.  Tonight it's dinner on "The Hill," the neighborhood where Yogi Berra grew up! Drury Hotel Maplewood - 2 nights (FB, L, D)

ArchDay 5

Day 5.

Take a break today in St. Louis.  Across the Mississippi River at Cahokia Mounds learn about a civilization in the Missouri River Valley from long ago, then walk over the Mississippi on the Chain of Rocks Bridge, once the route of old 66, back into Missouri.  This afternoon enjoy a special Route 66 treat, Ted Drewes Frozen Custard. (B, L)

CaveDay 6

Day 6.

St. Louis to Springfield, MO: The Meramec Caverns were opened to tourists in the 1930's, just above the time Route 66 made traveling to them easier.  In the late 1860's Jesse James used them as a natural hideout. The smooth path allows nearly all to explore.  Learn more about the local bank robber at the Jesse James Museum.

What follows is a marvelous stretch of The Mother Road, through Cuba (what beautiful murals) to Devil's Elbow into Ozark Country. Lunch is at one of our favorite roadside retreats, the Missouri Hick BBQ in Cuba.  There's also a stop at "Uranus," a unique roadside stop that isn't popular with everyone in town.  Finish the day in Springfield, MO, where Route 66 was "born." We'll celebrate The Main Street of America tonight by staying in one of the original accommodations (updated, of course) and dining at Steak 'n Shake! Best Western Rail Haven (B, L, D)

Panorama WaterDay 7

Day 7.

Springfield to Miami: On the way to Carthage is a most interesting spot, Red Oak.  This collection of buldings is practically a town...isn't it?  Who did this and why?  The nearby town square in Carthage is a true jewel, sporting a majestic courthouse, an interesting Civil War Museum (one of the first battles was right in this area) and a wonderful old-time soda fountain that affords us time for lunch.  After passing through Joplin, tiny Riverton is along the 13-mile stretch of Route 66 which cuts through the corner of Kansas, the shortest stretch of the highway in any single state.  Scott Nelson's small store is a perfect place to stop to find that special Mother Road souvenir.

In Galena, meet "Tow-Tator," who bears an incredible likeness to a tow truck in the Disney movie Cars named "Tow-Mater." In fact this is the old truck that inspired that character!  Tonight dine in the historic Coleman Theater, a 1929 landmark the town has successfully saved.  Hampton Inn (B, L, D)

Day 8.

Miami to Tulsa: Your first stop today is in Commerce, the hometown of Mickey Mantle.  We'll make a special presentation to the high school baseball team.  There's a park with giant cement Totem Poles, and then you'll arrive in Claremore to visit the Will Rogers Memorial, a tribute to America's famous humorist.  Lunch is special, with treats not afforded just any traveler as you'll see.  There's even a picture stop at the legendary Blue Whale on the way to Tulsa. Stay the night at historic Mayo Hotel, built in 1925. (B, L)

Day 9.

Tulsa to Oklahoma City: This was the home of Black Wall Street.  Something terrible happened here in 1921, just before the Mother Road was born.  A guided tour this morning will bring history to life. Leaving Tulsa, we come to Stroud and stop for lunch at the Rock Cafe.  There's a great story here! Just up the road in Arcadia is the Round Barn. Built in 1898, the barn is being restored to its original grandeur. At "Pops" you can choose your own afternoon refreshment! Embassy Suites (FB, L, D)

CapitalDay 10

Day 10.

Oklahoma City and Home:

Plan to depart for home on a flight about 3pm today. One more wonderful stretch of Route 66 first, however.  Our expert Oklahoma guide takes us to The Stockyards, then tells the story of the Dust Bowl and how it changed the lives of those in its path and sent tens of thousands to the "promised land" in California. (FB)

Daily Itinerary Meal Legend
CBContinental Breakfast
BGenerally a limited buffet or menu
FBFull buffet or choice of menu
BRBrunch, often buffet-style
LLunch, often several menu options
HT or ATHigh or Afternoon Tea
DDinner, often several menu options


Thursday, April 20, 2023 to Saturday, April 29, 2023

10 Days, 23 Meals

9 breakfasts, 9 lunches, 5 dinners

Many of them in classic restaurants - everything from roadside diners to fancy sit-downs in historic eateries


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