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Exploring Historic Route 66: Part 1

Originally Published in Trailer Life Magazine

As of November 11, 1926, the day it was officially designated, Route 66 became “the road on which America drove west.” At 2,448 miles, stretching from Lake Michigan in Chicago to the Pacific Ocean at Santa Monica, Calif., the two-lane road crossed eight states and three time zones, stitching the country together by linking the industrial regions of the Midwest with the golden plains and monuments of the West.

The highway was so well-traveled for the next few decades that it was dubbed the Main Street of America, as Route 66 literally ran along Main Street in the dozens of cities, towns, and hamlets it bisected.

It was also affectionately called “The Mother Road” (so-named by John Steinbeck in “The Grapes of Wrath”), though when it became a route of escape for thousands of desperate families fleeing the Depression and Dust Bowl during the 1930s, it did not treat the migrants tenderly; many broke down along the way, ran out of money and supplies or couldn’t find work in the “promised land,” California.

The 1940s changed travel on the route. During WWII it served as a military conduit, moving vast numbers of men, munitions, and equipment. And when the hostilities ended, a tourist boom began, when families on vacation rolled along America’s Main Street, propelled by Bobby Troup’s 1946 hit song, “Get Your Kicks on Route 66.” For years “getting there” was more important than “arriving” and Route 66, with gaudy neon signs lighting much of the way, was just the avenue for the trip.

My husband, Guy, and I drove the entire length of Route 66 with the help of maps by Route 66 historians/enthusiasts Jerry McClanahan and Jim Ross, half a dozen books on the subject and far better signage now than 10 years ago due to the renewed popularity of traveling the historic route and a fair amount of exploring on our own. We traveled the Route for one month, though RVers without that luxury of time can shorten the trip by traveling the interstates that for many stretches have supplanted the old road. Our trip will appear in a four-part series in Trailer Life. The first part of our trip covers the span from Chicago to Springfield, Mo.


Route 66 officially began in Chicago at the corner of Michigan Avenue and Jackson Boulevard. There is still a marker, but now Jackson Boulevard is a one-way going east. Bill Kelly, executive director of the Illinois Route 66 National Scenic Byway, suggests starting the trip at either the Chicago Art Institute or at nearby Clarence Buckingham Memorial Fountain in Grant Park.

We began at the fountain, a landmark since 1927. Twice the size but patterned after the Latona Fountain at Versailles in France, the magnificent Buckingham is designed to represent Lake Michigan, and includes four pairs of seahorses symbolizing the states that touch the lake: Wisconsin, Indiana, Michigan and Illinois. We suggest a walk around the lovely park for fine views of gray-green Lake Michigan and the hundreds of boats in the harbor, and opposite, the dramatic Chicago skyline.

You might encounter a few brief detours for road construction along the way, but Route 66 is well marked through Chicago, its suburbs, and the rest of Illinois as well. Illinois claims more than 400 miles of the historic route in several different alignments. Interstate 55 roughly parallels the old road the entire way.

Attractions are numerous. Among them is National Scenic Byway’s newly-installed kiosk in Berwyn, the first of 14 similar kiosks scheduled to be built between Chicago and St. Louis. Visitors read about the history of the road and listen to Troup’s famous tune.

Continue south to the White Fence Farm Restaurant, built nearly 90 years ago by Peabody Coal Company president Stuyvesant Peabody, who believed people would enjoy a simple menu of superior food served in an attractive farm atmosphere. The restaurant, famous for its fried chicken, became hugely popular after Route 66 was designated. The farm also includes a petting zoo.

Ahead is Joliet, a town that capitalizes on its Route 66 connection (frequent signs urge you to “Get Your Kicks on Route 66”). Be sure to stop at the Rich & Creamy, a frozen custard stand that opened in 1975. Life-size versions of Jake and Elwood Blues — “The Blues Brothers” — dance on the roof, and Joliet Correction Facility, which appeared in the opening scene of the movie, can be seen in the distance.

Route 66 Park adjoins the custard stand. Placards tell the old road’s story and note the locale of five historic gas pumps placed through the town at important sites. For example, a red and yellow Shell pump is here while another, an antique Texaco pump, is near the magnificent Rialto Square Theatre. The Rialto was built as a vaudeville palace in the 1920’s. The Rialto, featuring Corinthian columns, a decorated apse, and a 20-foot-long crystal chandelier, is the oldest theater on Illinois Route 66.

Continue south along Illinois Highway 53 (Old Route 66) toward Springfield. At Wilmington the 28-foot-tall Gemini Giant stands outside the Launching Pad, a drive-in restaurant. Another drive-in just ahead at Braidwood — the Polk-A-Dot Drive-In — is similarly eye-catching. Life-size Blues Brothers are dancing on one side, while Elvis, Marilyn Monroe, James Dean, and Betty Boop strike familiar poses along with the other.

Gardner, a lovely town with nearly 1,500 residents, is notable for its surprisingly fine two-cell jail built in 1906. Nearby is a 19th century horse-drawn streetcar that was converted to the Streetcar Diner in 1932. No food has been served since 1939, but the diner, now a museum, looks open for business.

Highway 53 ends at Gardner, but well-marked Old Route 66 continues south through a string of small towns, including Odell, which features a historic Standard Oil station, restored to its 1932 appearance, and now offering cold water, pop, and souvenirs. Elsewhere in town, across the street from St. Paul’s Catholic Church, is a reminder of the days when Route 66 was so heavily traveled that crossing on foot was hazardous. An underground passage, now filled in though the entrance remains, allowed churchgoers and school children to get across safely.

Ahead, Pontiac offers a particularly important stop on Route 66 today, the Illinois Route 66 Hall of Fame is located on the first floor of a fire station and was built in 1900. Nearby is the Pontiac-Oakland Automobile Museum, featuring a large collection of classic Pontiacs and Oaklands.

The capital of Springfield, Ill., is ahead. Attractions are plentiful, most of them Lincoln-related. Not coincidentally, our visit took place the last weekend in September, when for the 11th year, the International Route 66 Mother Road Festival was underway. The three-day event draws more than 80,000 visitors, many of who take part in a Friday evening “cruise” of Old Route 66. By early Saturday morning, some 1,100 classic cars and trucks are on display along 20 square blocks of the city.

Of the dozens of restaurants in Springfield, one Route 66 travelers should not miss is Cozy Dog, which was founded in 1950 by Jennie and Edwin Waldmire and is still in the family. Grandson Tony Waldmire now runs the restaurant best known for its “cozy dogs” (Don’t call them “corn dogs,” Waldmire says with a smile), but the menu is extensive.

South of Springfield you have two choices: follow the original (1926-30) Route 66 alignment on Illinois Highway 4 or the later (1930-43) alignment, which closely parallels I-55; signage is excellent. We drove both routes but preferred the longer-but-more-interesting, pastoral Highway 4, which also strings together numerous small towns, but in addition offers short side-trips on the earliest sections of road, one of them laid brick.

Henry’s Rabbit Ranch and Route 66 Emporium, run by Rich Henry, is on the newer alignment at Staunton and we recommend a stop. Henry, who was named to the Illinois Route 66 Hall of Fame in 2012, built his establishment in 1922 “to look like an old-time service station.”

The name “Rabbit Ranch” is derived not only from the seven upended VW Rabbits “planted” outside (similar to Cadillac Ranch in Texas) but also from the numerous pet rabbits Henry has rescued from shelters. He currently has 14, most in large cages. Big Red, an enormous rabbit with the softest fur you can imagine, is the exception, spending his days lounging on the shop’s counter as the “official Route 66 greeter.”

South of Staunton Old Route 66 leaves Highway 4 to follow the frontage road to Illinois Highway 157 at Hamel. The route continues south on Highway 157 through Edwardsville, then crosses South University Drive to become Chain of Rocks Road into Mitchell.

There, the restored Luna Café, now a bar rife with Route 66 memorabilia, was once a supper club frequented by gangster Al Capone. A restored neon sign shaped like a cocktail glass advertised the establishment, and when the neon cherry at the bottom of the glass was lit, that meant ladies at the upstairs “house of ill repute” were also open for business.

There is no single route into or through St. Louis — the biggest city between Chicago and Los Angeles — on the route the alignment was changed so often over the years. Two of the three bridges that at various times carried the old highway across the Mississippi are no longer open to auto traffic.

However, mile-long 1929 Chain of Rocks Bridge, part of a route to bypass the city from 1936 till 1968, has been restored and was added to the National Register of Historic Places in 2006. The erector set-like old toll bridge, among the more unusual structures to span a river due to the 22-degree bend in the middle, is popular for walking and bicycle riding. Placards and replicas of Route 66 postcards tell the story of the bridge, now part of the Route 66 Bikeway, linked to more than 300 miles of bike trails on both sides of the river.

Continue south on Illinois Highway 3 to the McKinley Bridge, built in 1910 as a railroad bridge. Auto traffic was added later, and the McKinley, the “world’s largest electric bridge,” was the first bridge on which Route 66 crossed the Mississippi into downtown St. Louis.

St. Louis abounds with major attractions, including more than six dozen that charge no admission (second only to the nation’s capital in numbers of free attractions). However, we recommend leaving the RV at a campground while touring the city; a good choice is the campground at the Casino Queen.

The Gateway to the West is famous for its fine eateries, and they are numerous. Two, in particular, are long associated with Route 66 — the Eat-Rite Diner and Ted Drewes Frozen Custard; as you leave St. Louis on the historic route (see map for directions).

The Eat-Rite opened as a donut shop in 1908 (two blocks south of Busch Stadium). Favorite dishes at the 24/7 diner include fried chicken; chili; sliders; and the St. Louis-original slinger, a hamburger patty topped with a fried egg, hash browns, chili, cheese and onions. A few miles west is Ted Drewes, founded in 1929 and renowned way beyond St. Louis for its concretes, blended frozen custard drinks so thick they don’t spill when turned upside down. The shop, on Route 66 and in its current building since 1941, recently introduced the Root 66 concretes named for the highway and the root beer it includes.

Along the old highway to the West is the site of the famous Coral Court Motel, now demolished but once a bustling “no-tell motel” (the 25 two-unit buildings all had attached garages), and the finest example of Streamline Moderne motel architecture on Route 66. One unit was saved and is partially rebuilt at the National Museum of Transportation.

Cutting a diagonal furrow across Missouri, Route 66, which followed the much-earlier Osage Indian Trail, became today’s I-44.

The 200-or-so mile drive through this lush rural landscape, limestone hills thickly statured with jade-hued oaks and cedars, is one of the loveliest stretches on the entire route. There are also numerous reasons to stop, with Meramec Caverns (a Jesse James hideout) near Stanton among the best. There is also the whimsical, such as the World’s Biggest Rocking Chair (42 feet tall, 20 feet wide) at Fanning’s “66 Outpost,” a Route 66 memorabilia shop in “Mural City” Cuba.

Evidence of interest in the old road is everywhere. Signs advertise Route 66 Antiques, Route 66 Gas, Route 66 Bar and BBQ Pit, Route 66 Antique Mall and Route 66 Motors, among others. At Route 66 Motors near Rolla, owner Wayne Bales displays century-old gravity gas pumps, a large red Pegasus, an array of historic autos and other Route 66 memorabilia.

The old highway diverges south from I-44 at Devil’s Elbow on Teardrop Road, runs through Hooker Cut, once one of the deepest rock cuts in the country, and crosses an especially scenic bend in the crystal-clear Big Piney River. You can drive the 1923 bridge (if your RV is less than 13 feet 8 inches high), but we also walked it.

The main attraction in Devil’s Elbow, a town founded in 1870 and named for the bend in the river, a “devil of an elbow,” is the Elbow Inn, a popular barbecue establishment. Outdoor seating is available on a patio overlooking the picturesque Big Piney.

West of town, the old highway climbs steeply to a pull-off at a scenic overlook. There we met Kim and Jytte Broberg from Denmark, who were devoting 26 days to driving Route 66. Kim explained that American history can be told through the roadways adding, “Route 66 is the most interesting — it’s famous all over the world.”

The old highway continues west, looping back and forth across the interstate, through the towns of Buckhorn, Hazelgreen, Lebanon (century-old Independent Stave Company here offers tours), and into Springfield, last stop on this first leg of our Route 66 odyssey.

It was in Springfield on April 30, 1926, that the name of the new Chicago to Los Angeles highway was first proposed, making the town the “official birthplace” of Route 66. A dozen years later it would become the first completely paved transcontinental highway in the country.

See more photos and points of interest here!

For More Information:

Illinois Route 66 Association
815-844-4566, www.il66assoc.org

Illinois Route 66 National Scenic Byway
217-525-9308, www.wayside66.irswebsolutions.com

Heritage Corridor Convention and Visitors Bureau
800-926-2262, www.heritagecorridorcvb.com

Illinois Office of Tourism
800-226-6632, www.enjoyillinois.com

Missouri Route 66 Association
417-865-1318, www.missouri66.org

Missouri Department of Tourism
800-519-2100, www.visitmo.com

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