Road Trip: Route 66

Get your kicks on Route 66 and experience the ultimate all-American road trip from Illinois to California.

They say driving Route 66, the iconic 2,400-mile road connecting Chicago with Santa Monica, sneaks us into a bygone America, an era of neon signs and mom-and-pop diners. This waits for us, just off the interstate. Right?

That may be true about the route, but that's not the only reason to take it.

"It's [more than] nostalgia, '57 Chevys, and James Dean," says Michael Wallis, a Route 66 lifer and author of Route 66: The Mother Road, which helped spark a 66 renaissance in the '90s.

"The real adventure is that it's unpredictable. There's this feeling of excitement, of almost danger that you can't get on the interstates," Wallis tells me by phone from his home in Tulsa, where he can see Route 66 from his window. "You go into some greasy spoon and [don't] know what you're going to get."

Often that's a bond made with the folks you meet. Or just finding the pie of a lifetime.

From the get-go of its opening in 1926, Route 66 has been a celebrity. Other highways crossed the country too, but only the "Main Street of America" had John Steinbeck's attention (with The Grapes of Wrath), an iconic soundtrack—"(Get Your Kicks on) Route 66"—and the ability to continue winning new hearts (via Pixar's Cars).

You can see how it earned its star status if you take it slow rather than "scoot and shoot" (local parlance for snapping photos from car windows and zooming off). The full trip, which winds on and off five interstates, requires at least two weeks. If you have less time, consider cherry-picking some areas to explore. Here are a few to help you get started.

Cozy Dogs, Springfield, Illinois

The family-run Cozy Dog Drive In has been serving corn dogs, or what they call hot dogs on a stick, in Lincoln's hometown since the '40s. The $1.95 dogs sizzle fresh from 8 a.m., when locals come to chat over coffee. You should linger to (digest and) take in the Robert Crumb-inspired artwork of the road by late family member Bob Waldmire.

Funks Grove Pure Maple Sirup, Shirley, Illinois

Illinois Funks have been selling their hand-tapped “sirup”—as syrup without sugar used to be known—from their grove of maples here since 1891, offering a rare Route 66 souvenir that actually predates the road. A good time to come is early March, when frozen sap thaws and drips into hanging buckets. Old school, as always.

Chain of Rocks Bridge, Illinois-Missouri Border

Before making the drive across the Mississippi into Missouri on the Chain of Rocks Bridge, walk it. Built in 1929 with a unique 22-degree angle partway across, the bridge faced an uncertain future not too long ago. Fortunately, Trailnet converted it into a walk-and-bike trail, connecting riverfront trails in both states.

The Loop, St. Louis

Over the past 40 years, the Delmar Loop, located a couple of miles off the road, has transformed from a drug den to an entertainment district with an eye on the past. The hub is Blueberry Hill, a buzzing, pub-style joint with memorabilia (original Beatles dolls, vintage jukeboxes) and a good burger. Its biggest claim to fame comes once monthly, when 87-year-old hometown hero Chuck Berry plays the basement Duck Room. Go early and you can get a front row seat.

Meramec Caverns, Missouri

Missouri's limestone bedrock is dotted with over 6,000 caves, but the most popular one is hard to miss. Advertised by painted barn tops along Route 66 (and I-44), the 4.6-mile Meramec Caverns has lured road-trippers since 1935. Much ado is made about Jesse James supposedly hiding out here.

Munger Moss Motel, Lebanon, Missouri

"Everyone's happy on Route 66," according to Iowan transplant Ramona Lehman, who runs Lebanon's classic Munger Moss Motel with her husband. "Because everywhere you go, it's people talking to people." Fond of spinning yarns herself, Lehman can point you to another place for chatting up locals—the epic Elbow Inn Bar, set on a wild bend of the Big Piney River known as Devil's Elbow. Add another day to canoe the waterways here. The Ozarks are gorgeous.

Tulsa's Brady District

Across the tracks from downtown, the revitalized Brady District gives the best sense of Tulsa's 66 era. You can catch a show at the ever present Cain's Ballroom, where Bob Wills housed his Western Swing in the '30s, and visit its new neighbor, the Woody Guthrie Center, to learn how Guthrie's "This Land Is Your Land" served as a leftist rebuttal to "God Bless America."

Rock Cafe, Stroud, Oklahoma

A highlight of the approximately 120-mile, land-hugging ride between Tulsa and Oklahoma City is Stroud's Rock Cafe, which has been here since the '30s, returning from a 2008 fire with gusto. Owner Dawn Welch, who inspired the Sally Carrera character in Cars, once chose to live in Stroud over Costa Rica. "Here I can have the world come to me, and we can slow down in each other's company," she says. "Who wouldn't want that every day?" Get the peach cobbler.

Route 66 Museum, Clinton, Oklahoma

"People in Clinton will not ever let go of their highway," Michael Wallis writes of this western Oklahoma town. A handful of 66-era motels and diners prove the point, along with the Oklahoma Route 66 Museum, a modern collection featuring donated knick-knacks. While you're in Clinton, grab some beef jerky from the oversize shack at Jiggs Smokehouse.

Palo Duro Canyon State Park, Texas

True, cars poke out from the cattle-country soil at Amarillo's Cadillac Ranch, but detour south and you'll find a bigger surprise: the Lone Star State's "grand canyon." About 30 miles southeast of Amarillo, the grasslands suddenly drop 800 feet at the 120-mile-long Palo Duro Canyon. You can stay in rustic New Deal-era cabins that lured Route 66 travelers of old; plus, in summer there's a fun cliffside production of Texas, sort of the state's rebuttal to Oklahoma!

Overnight in Tucumcari, New Mexico

Follow the iconic "Tucumcari Tonite" signs for a serious way-out-there vibe. A good place to start is the historic coral-and-sky-blue Blue Swallow Motel, a 12-unit place with a cozy courtyard to take in the big sunsets. "It's really cool to see what happens," says Michigan transplant Nancy Mueller, who runs the motel with her husband, Kevin. "People from all parts of the world sit here, talk, drink wine, listen to the neon buzz. Sometimes they end up traveling together."

Some head over to the just renovated Odeon Theatre open since 1936. Owner Robert Lopez, a local cotton farmer, used to bring dates here. "Everyone in Tucumcari does," Lopez says. "It's the only place you can go."

El Morro National Monument, New Mexico

Before Route 66 came around, over 2,000 trailblazers passed this way, carving their names on the base of a 200-foot-high sandstone questa. At El Morro National Monument, a detour via Hwy 53 from Grants, you can see Native American petroglyphs of bighorn sheep, birds, and lizards that date back seven centuries. Also here are marks left from Don Juan de Oñate, the colonizer who conquered the pueblo at nearby Acoma. He wrote his name here on April 16, 1605—right on top of a petroglyph.

Meteor Crater, Arizona

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You don't have to believe in UFOs to believe in the extraterrestrial. Particularly not at this longtime Route 66 attraction. About 50,000 years ago, a meteor about half the size of a football field crashed here, leaving a nearly mile-wide crater you can tour on a guided hike. And, hey, Elvis liked it.

Seligman to Kingman, Arizona

The 85-mile stretch of Route 66 bends (and bends) past sagebrush, rugged mountains, and ranchland before passing a '57 Corvette and a couple dozen old cars. This is the Hackberry General Store, a makeshift Americana museum run by Tacoma transfer Thurston Pritchard. In 1998 his parents—big-time collectors—spotted a house filled with snakes, rats, and "hippie" artist Bob Waldmire. They made him an offer. Inside you'll see Waldmire's parting gift, a wall mural of Route 66 and a ceiling's worth of donated license plates (the snakes and rats are gone). "Visitors walk in and go, 'oh my god, it's like another time. It even smells old in here,'" says Thurston.

Oatman, Arizona

For "a truer sense of being alone," per Route 66 writer Tom Snyder, take the wild road west from Kingman past saguaro cacti and loose boulders. It leads to a terrifically weird place: Oatman, an old gold-mining town that persists only because it's gone camp. Descendants of abandoned burros beg for carrots (sold locally), staged gunfights appear daily (at gift shops), and you can eat at the 1902 Oatman Hotel (supposedly frequented by Clark Gable).

Needles, California

"Oh gosh," says Needles native Don Rupe. "That river is a big calling when it's 115 degrees out." He speaks of the Colorado River, a refreshing spot that lures locals, as it did the Joads in The Grapes of Wrath. You can get in at Jack Smith Park. Afterward pay a visit to El Garces, an iconic hotel and train station that dates to 1908. The pillared building has been under renovation for years and reopens in May 2014 to eventually receive wee-hour Amtrak trains.

Wigwam Motel, Rialto, California

The approach of the mighty sprawl of metropolitan L.A. doesn't mean the ride's over. Just past San Bernardino, as the cityscape takes over, this kid-friendly motel is the best of the three remaining "wigwam" motels that appeared in the '30s, '40s, and '50s. And even if you ignore their infamous sign ("Do it in a teepee"), it's worth stopping for a night. Each concrete room is well kept up and faces a palm-dotted lawn with a pool.

Will Rogers State Historic Park, Los Angeles

A plaque for the Will Rogers Highway in Santa Monica's Palisades Park marks Route 66's unofficial end—the real one was buried by a freeway ramp at Lincoln and Olympic Boulevards. The plaque pays tribute to Rogers, an Oklahoma native who found fame via the Mother Road. At the nearby Will Rogers State Historic Park, you can tour his ranch, hike mountains overlooking the Pacific, and ponder his quip that the Dust Bowl immigration of Okies to California "raised the average intelligence of both states."

Robert Reid is National Geographic Traveler's Offbeat Observer. He grew up in Tulsa and regularly takes Route 66 to Oklahoma City because it's so great—and to beat the $4 toll.

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