Route 66 is "an archeological dig of over 2448 miles, through over 7 decades of roadside Americana," writes Jerry McClanahan, artist and author of EZ66, the bible of "Mother Road" trip planning. It’s nostalgia by way of gleaming retro service stations, quirky artists, towns once overrun with outlaws and diners with neon signs that appear on the horizon like a mirage.

"The first thing to understand is that you are at your destination wherever you are," explains Swa Frantzen, founder of Historic66.com. "The race to the finish ruins the experience." With some exceptions, Frantzen recommends making less than 200 miles of "progress" a day.

We'll follow the traditional westward route from Chicago to Santa Monica, with highlights, tips and B&B recommendations along the way.

 


 

Illinois: The Land of Lincoln

Illinois: The Land of Lincoln

Don’t blink or you’ll miss one of a few Route 66 start signs in Chicago, a no-brainer destination for a pre-trip idle. Be sure to fuel up at the popular Dell Rhea's Chicken Basket, a family roadhouse with 80+ years in the bird-frying business.

History buffs shouldn't miss Springfield, Illinois. Make time to visit the Abraham Lincoln Presidential Library and Museum and pay your respects at his final resting place.

In Staunton, you’ll find one of guru Jerry McClanahan's favorite stops, Henry's Rabbit Ranch, which marries the metallic chill of a half-sliced-VW-rabbit graveyard and a farm with actual warm-blooded bunnies.

 

Perfect B&B Pit Stops

Villa D'Citta

Villa D' Citta

Chicago, Illinois

Built in 1887 as a summer cottage, Villa D' Citta is a boutique mansion in Chicago's thriving Lincoln Park. A highlight: a fridge stocked with eggs, ham, Italian salami and cheeses to combine with fresh Italian bread, tomatoes and peppers.

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Rippon Kinsella

The Rippon-Kinsella House

Springfield, Illinois

Set up shop within walking distance of Oak Ridge Cemetery and Lincoln's Tomb (plus easy access to additional historic sites downtown).

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Missouri: The Show Me State

Missouri: The Show Me State

They've got their eye on you at Laumeier Sculpture Park & Museum, an outdoor gallery featuring more than 60 photogenic installments, including a massive blue eyeball that seems to gaze, unflinchingly, into your soul.

Up the road, Route 66 icon Gary’s Gay Parita features a replica 1930s service station, the requisite collection of vintage car curio and plenty of road trip lore from the friendly operators. But the #1 pick for Missouri — of one road trip acolyte, at least — is the Route 66 Red Rocker. Austin Whittle, founder of theroute-66.com, is enamored by the 42-foot-tall rocking chair, which serves as a reminder to sit a spell.

 

Perfect B&B Pit Stops

Brewer House

Brewers House

St. Louis, Missouri

Shack up at a Civil War era home located just a hop from several breweries and 1.5 miles from downtown St. Louis.

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Walnut Street Inn

Walnut Street Inn

Springfield, Missouri

The Queen Anne Victorian mansion in the heart of the Ozarks features four-poster beds, clawfoot soaking tubs and antique flourishes.

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Kansas: The Sunflower State

Kansas: The Sunflower State

Sneeze and you'll miss the 13-mile intermission in Kansas. It's an interesting segment, nonetheless. It was the first part of the Mother Road to be paved in 1926 and includes a number of novelties like Cars on the Route — a restored 1920s-style fill-up station — and abandoned buildings that tell stories of the Civil War cattle drives and lead mining.

 


 

Oklahoma: The Sooner State

Oklahoma: The Sooner State

On this open stretch of great plains, you'll pass through Oklahoma City, home to the National Cowboy and Western Heritage Museum, and the Oklahoma City National Memorial & Museum, a poignant stop honoring those affected by the 1995 bombing.

On the lighter side, how does a husband express his love to his wife? If she collects whale figurines, so the tale goes, the man builds her a grinning sculpture of the largest animal in history. Hugh Davis' Blue Whale of Catoosa has since become one of the most photographed images on 66.

Hungry? McClanahan says to get your grub on at another Mother Road staple: Stroud, Oklahoma’s Rock Cafe, serving up spaetzle, schnitzel and chicken fried steak. And don’t forget the pie.

 

Perfect B&B Pit Stops

Cedar Rock Inn

Cedar Rock Inn

Tulsa, Oklahoma

Situated on a 55-acre farm, this 120-plus-year-old sandstone mansion offers rustic luxury in a park-like setting.

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Texas: The Lone Star State

Texas: The Lone Star State

Next, you'll roll through 150+ original Route 66 miles of the Texas Panhandle, covering barren Martian-red flatlands where tumbleweeds go to retire. This entrée into the Wild West features retro service stations and colorful downtowns with yet more stories to tell.

But the marquee stop in Texas is Amarillo's Cadillac Ranch, a mysterious row of spray-painted, half-buried Caddies, tailfins angled toward the sky, from whence they seem to have crash landed in an explosion of tie dye.

If your stomach is running on empty, hit Amarillo's landmark Big Texan Steak Ranch, where consuming a 4.5-pound slab of beef (and sides) in under an hour means the meal — but not the medical bill — is on the house.

 

Perfect B&B Pit Stops

Three Falls Cove

Three Falls Cove

Amarillo, Texas

There aren't many B&Bs on this lonesome stretch, but the serene Three Falls Cove, 50 minutes from Amarillo, is set on a (surprisingly) green plot with trails and a stocked pond.

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New Mexico: The Land of Enchantment

New Mexico: The Land of Enchantment

This is the start to the trip's most scenic expanse, covering craggy red rock mesas and desert landscape. As you collect experiences from the road, New Mexico's state motto — Crescit eundo, "it grows as it goes" — starts to come into view.

Multiple 66 devotees recommend an extended stop in Tucumcari, originally a Southwestern railroad encampment notorious for gunfights. The days of its "Six-Shooter Siding" nickname are gone, but quirky Tucumcari Historical Museum keeps the memories alive all the way back through prehistory. Nearby, Tee Pee Curios, a favorite shop for 66 and Southwest souvenirs, offers funky jewelry, mugs, T-shirts and homemade aprons.

And then it's off into what seems like another mirage: the Blue Hole of Santa Rosa, an 80-foot-deep, azure-blue swimming spot that even offers scuba diving in its refreshing mid-60˚ depths.

66 continues through both the art-gallery-laden Santa Fe (original 1926 route) and/or Albuquerque (rerouted in 1937), NM's population center boasting Pueblo cultural attractions and plenty of dining options.

 

Perfect B&B Pit Stops

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Bottger Mansion of Old Town

Albuquerque, New Mexico

This ideally located B&B — near restaurants, shops and galleries — earns rave reviews for its breakfast offerings, including a blueberry French toast casserole.

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Four Kachinas

Four Kachinas Inn, Santa Fe

Santa Fe, New Mexico

This six-room compound in a garden setting is tastefully decorated in Southwestern style.

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Arizona: Grand Canyon State

Arizona: Grand Canyon State

This 400-mile segment of 66 covers a bounty of must-see attractions, including Petrified National Forest; several Indian trading posts; the town of Seligman, featuring one of the route's most vibrant, preserved-in-amber main streets; and the "living" ghost town of Oatman, a kitschy village co-inhabited by humans and burros.

Halfway across the state, you'll hit Flagstaff, a prime base camp for an off-route adventure to the Grand Canyon, the most popular side trip.

Arizona also claims some of Mother Road's most highly touted cooking — Frantzen and McClanahan raved about the Turquoise Room in Winslow, Arizona. Creative menu options include Southwest flavors like chilaquiles, bread pudding with prickly pear cactus and pork carnitas. (Classic rock fans will also recognize the town from the Eagles' "Take it Easy.")

 

Perfect B&B Pit Stops

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Starlight Pines Bed & Breakfast

Flagstaff, Arizona

A great multi-day base for exploring the Grand Canyon, the inn features 14-foot vaulted wood ceilings, a large wraparound porch and three canine companions.

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California: The Golden State

California: The Golden State

The superlative scenery continues through the Mojave Desert and along the Colorado River, by vintage cafes with still-beaming neon signs. Then there's Elmer's Bottle Tree Ranch, where an artist with a vision has grown a beguiling glass-and-wood forest with bottles as "leaves."

One of Frantzen's favorite under-the-radar 66 stops is the Los Angeles Theater on Broadway, with a gorgeous interior and a façade "that screams for attention."

The road trip ends, if it ever really does, with the famous Santa Monica Pier, where the original 66 reaches the palm-tree-lined Pacific — and you take a moment to get nostalgic about all the nostalgia.

 

Perfect B&B Pit Stops

Inn at Playa Del Rey

Inn at Playa Del Rey

Los Angeles, California

An urban inn featuring free bikes, afternoon wine and a great view of the Marina del Rey.

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Hollywood Bed & Breakfast

Hollywood Bed & Breakfast

Los Angeles, California

1912 B&B located on Hollywood Blvd within walking distance of the Sunset Strip, Walk of Fame and Grauman’s Chinese Theater. Plus, it has a pool.

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Explore the whole route: