Route 66: one legendary road, plus two big birthdays

Route 66 turns 100, the U.S. turns 250--it's one unforgettable trip!

If you’re looking for a sign to hit the road, this is it—painted on vintage billboards, lit up in neon, and maybe even shaped like a giant blue whale. In 2026, America is throwing a double birthday bash: the U.S. turns 250, and Route 66—the highway of honky-tonks, heartland diners, and hair-raising roadside attractions—celebrates its 100th anniversary.

Here’s one nostalgic, joy-filled way to mark the moment: a guided Route 66 Westbound tour.

Two milestones, one iconic road

Route 66 isn’t just a highway—it’s a rite of passage with tailfins, chrome, and maybe a few Elvis sightings (cardboard or otherwise). This is the original road trip dream.

Commissioned in 1926, the Mother Road stretched from Chicago to Santa Monica, linking small towns and big dreams. And it just so happens the U.S. turns 250 in the same year that Route 66 turns 100, making this the ultimate Americana moment—celebrating history, freedom, and a whole lot of quirky.

Itinerary: Route 66 westbound

Available dates: May 19 or May 31, 2026 – check with me for additional options after that

From the skyscrapers of Chicago to the shores of the Pacific, this 12-day guided adventure covers over 2,000 miles of legend, lore, and lovingly preserved weirdness.

Start in Chicago & southern Illinois

• Kick off your journey in the Windy City, then cruise past muffler men, classic diners, and Abraham Lincoln’s stomping grounds in Springfield.

• Pro tip: Your camera will get a workout before you even leave Illinois.

Missouri to Oklahoma: roadside glory

• Stretch your legs at Meramec Caverns (Jesse James’s hideout!), pop into quirky museums, and wave at the world’s largest rocking chair.

• Taste test every slice of pie in sight—there are no rules (and no calories on vacation).

Texas to New Mexico: desert flair

• Hit the Cadillac Ranch (yes, the one with the cars buried nose-first in the dirt).

• Stay in retro motels with turquoise doors and neon signs that practically hum with 1950s charm.

• Tucumcari, NM: known as the “gateway to New Mexico, and home to the vintage Blue Swallow Motel

Arizona: nostalgia dialed up to 11

• Cruise through Seligman, the inspiration for parts of Disney’s “Cars” movie.

• Route 66’s past lives on here, in pastel motels and drive-ins with a sense of humor.

California dreaming: end of the line

• Cross the Mojave and roll into Santa Monica with the wind in your hair (convertible optional).

• Celebrate at the pier—after 100 years, the road still ends with a beach view.

Inclusions

This tour includes a smooth ride in a Mercedes Benz Sprinter van, professional tour guide, all of your hotel stays, most of your meals, many entrances & tours, gratuities for meals & activities, transportation from the airports, and much more.

A few fun facts for the ride

• The number “66” was picked because it sounded catchy—and it stuck. Marketing genius, 1920s-style.

• John Steinbeck called it “The Mother Road” in The Grapes of Wrath, and America never looked back.

• Route 66 was decommissioned in 1985—but the diners, motels, and dancing cactus signs didn’t get the memo.

• Some of the most beloved stops: a giant ketchup bottle, a curiously grinning jackrabbit, and a ghost town that hosts more photographers than people.

Ready to roll?

This is more than a tour—it’s a love letter to roadside America, written in motel postcards and sung in diner jukeboxes. You’ll make memories, snap photos that feel like time travel, and celebrate two historic birthdays with one unforgettable trip.

What’s your dream Route 66 stop—the classic Blue Swallow Motel in Tucumcari, NM? Cadillac Ranch? Or just cruising with no particular place to go? Let me know if you’d like more info about this iconic celebration! I can get you all the details. Contact me IMMEDIATELY for an extra bonus discount on this trip!