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Dubbed “The Mother Road” by John Steinbeck, this iconic highway has inspired generations of Americans to take to the open road and go traveling.

By Trina Kaye

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Times may have changed, but Route 66—the highway some folks believed was dead and gone—is alive and kicking like never before. One book gives you everything you need to know about this iconic highway. The new ROUTE 66 ADVENTURE HANDBOOK: High-Octane 5th Edition (Santa Monica Press/May 2017), by Drew Knowles contains new and interesting facts as well as maps to guide riders down the multiple paths of Route 66, displaying the exact locations of points of interest.

Route 66 begins in Illinois, near the shore of Lake Michigan. Of course, one can just as easily begin a tour of Route 66 from its western terminus in California, but there are good reasons not to. Traditionally, the Mother Road runs westward, from Chicago to Santa Monica, just as the United States of America has always been a westward-moving nation.

The U.S. began as a small grouping of states huddled along the Atlantic coast. To the west, the future states of Kentucky and Tennessee were wildernesses. Ohio and Indiana were settled by a few intrepid farmers for the value of their soil. Illinois was at that time considered the Northwest, and about as far west as any “American” semblance of civilization that existed. Over the generations, more and more of that West has been tamed, and the outposts of civil society have moved westward as well.

Traveling Route 66 from east to west, then, you will be following the well-worn path of this country’s very development. The countryside will unfold before you, just as it did for the American people in their conquest of the continent several generations ago, almost as though you had mastered time travel. You will be richer for the experience, because you will come away feeling a kinship for the brave souls who pushed America’s boundaries and made her what she is today.

Inseparable from the story of westward movement is the availability of water, as both transportation and sustenance. The development of Chicago as the outpost of civilization that it came to be was largely due to its location at the far end of a string of lakes and other navigable watercourses. For many reasons, water sources are conducive to settlement, while a scarcity of water is a severe hindrance to any development. It is no accident, then, that Chicago, St. Louis, and Los Angeles are the largest cities on Route 66—they are located at the route’s three largest water sources: Lake Michigan, the Mississippi River, and the Pacific Ocean, respectively.

As you move westward on Route 66, the story of water is one which the observant traveler will read all along the way. West of St. Louis, there is a gradual decrease in water availability and a simultaneous decrease in population density. The rivers that Highway 66 encounters are smaller, and the cities that dwell on the banks of those rivers are proportionately smaller as well.


The famous Chicago fire of 1871, which may or may not have been caused by Mrs. O’Leary’s cow, utterly destroyed the city. Afterward, the city made a conscious effort to rebuild using more durable materials and superior building methods so that the new Chicago would stand the ravages of time and nature. More than a century later, the city continues to take pride in its architecture. If you are at all interested in the art and science of architecture, it is worth your while to take advantage of some of the countless tours available. Some of the most well-known tours take place on the water, and launch from either the Chicago River or Lake Michigan. Other tours, which can be taken by bus, air, trolley, or bicycle, are also available.

Chicago was the scene of the World’s Columbian Exposition in 1893, the grounds of which were designed by Frederick Law Olmstead, who also designed New York’s Central Park, the Stanford University campus, and other acclaimed outdoor spaces. It was at the 1893 Exposition that George Washington Gale Ferris introduced the now-familiar Ferris wheel. The original was 250 feet tall and had 36 cars, each with a capacity of 60 passengers. That original wheel was later moved and used at the 1904 World’s Fair in St. Louis. The two lions that graced the Exposition’s Palace of Fine Arts building have since been made a part of the Art Institute of Chicago, near the spot where westbound Route 66 begins.

The Exposition of 1893 made some other memorable or even permanent imprints. It was there that Cracker Jack was first introduced, later immortalized in the 1908 song “Take Me Out to the Ball Game.” Little Egypt, otherwise known as Catherine Devine, scandalized the fair by performing the hoochee-coochee in scanty attire (some say in the nude). The model for Aunt Jemima, a woman named Nancy Green, was a cook who advertised food products at the Exposition. Visitors enjoyed the first-ever public use of electric lighting at the Exposition, and it was also the scene where hot dogs were first served on buns. The vendor, A. L. Feuchtwanger, handed out white gloves with the sausages so that his customers’ hands wouldn’t be scalded. To his initial dismay, the gloves were not being returned as he had intended, and so he began substituting bread instead.

Chicago once had a less-than-savory reputation as the home of the underworld. Gangland slayings were not uncommon. The infamous St. Valentine’s Day Massacre occurred in 1929 at the SMC Cartage Company at 2122 Clark Street. The building was demolished shortly after its use as the set for the 1967 film starring Jason Robards and George Segal.

Outlaw John Dillinger was gunned down by law enforcement officials on July 22, 1934, outside the Biograph Theater (2433 N. Lincoln Avenue). Dillinger had just viewed a gangster film there called Manhattan Melodrama. There is a plaque at the site to mark the occasion. The leader of the FBI contingent was Melvin Purvis, who committed suicide in 1960 using the same pistol given to him by his fellow officers to commemorate Dillinger’s violent end.

In 1933, Chicago played host to the Century of Progress Exposition. It was there that Sally Rand made her splash by riding a white horse to the fair “attired,” more or less, as Lady Godiva. Her main act consisted of an essentially nude dance routine, which included the strategic use of ostrich feathers. This caused such a sensation that she was able to parlay it into a career which lasted some thirty years.

The 1933 Exposition also brought the first aerial tramway, the first public demonstration of stereophonic sound reproduction, and the debut of Grant Wood’s now-famous painting, American Gothic. A former student at the Art Institute of Chicago, Wood intended for his painting to be a sort of spoof of the Holbein style.

Chicago Attractions

Following is just a small sampling of local offerings that you might find interesting if you plan to spend significant time in America’s “Second City” and its immediate surroundings.

The Chicago Water Works (163 E. Pearson St.) tower was one of the few structures in Chicago to survive the 1871 fire. It now houses a visitor center where you can purchase half-price day-of-performance theater tickets. There is also a gallery of photographs by some of Chicago’s own native talent, as well as other welcome amenities.

The Chicago History Museum (1601 N. Clark St.) is the city’s oldest cultural institution, established in 1856. The museum traces the city’s development from outpost through the present day, with a permanent display pertaining to America in the Age of Lincoln. Also included is a passenger car from 1893, on which the public traveled to the World’s Columbian Exposition that year.

Dearborn Station (47 W. Polk St.), a National Landmark in the Romanesque style dating to 1885, has been converted to a mall and marketplace.

The Charnley-Persky House Museum (1365 N. Astor St.), formerly a residence, was a joint project by Louis Sullivan and protégé Frank Lloyd Wright in the early 1890s.

Dating from the early 1880s, the Pullman Historic District is the country’s first planned industrial community. Guided walking tours are available at the Historic Pullman Visitor Center (11141 S. Cottage Grove Ave.) Within the district are the Greenstone Church, the Hotel Florence Museum, and the A. Philip Randolph Pullman Porter Museum Gallery. The Pullman Porter Museum features an outstanding collection of historical photographs.

The Prairie Avenue Historic District includes the Clarke House Museum (1827 S. Indiana Ave.), a Greek Revival design that is the oldest residence in the city (1836). The Glessner House Museum (1800 S. Prairie Ave.) is nearby.

The residences in the 3800 block of Alta Vista Terrace are a little bit peculiar. Each house on one side of the street has a twin (with only minor variations) on the opposite side of the street, in exactly the same order. However, since the two series begin at opposite ends of the block, only in the center of the block do the designs directly across from one another match.

Chicago’s Hotel Intercontinental (505 N. Michigan Ave.) started out in 1929 as the Medinah Athletic Club, and its world-class, lavishly decorated swimming pool is where Olympic gold medalist Johnny Weissmuller did some of his training during his years portraying Tarzan on the big screen.

The Tribune Tower (435 N. Michigan Ave.), which houses the famous newspaper, was completed in 1925 following a design competition among several distinguished architectural firms. The building includes fragments of some 120 architectural icons from around the world embedded in its walls, including the Taj Mahal, Palace of Westminster, and Great Wall of China.

Accessible through a subway-like entrance across from the Tribune building is the Billy Goat Tavern (430 N. Michigan Ave.), made famous by Saturday Night Live’s “cheese-boiga” routine.

Speaking of eateries, Chicago has myriads of them. But one of the more out-of-the-ordinary ones is the Weber Grill Restaurant (539 N. State St.). All meals are prepared on actual Weber-manufactured grills, much like one you may have at home. They’re fired by charcoal, just like yours, and you can watch your food being prepared in “backyard” fashion. Surrounding the patio is a railing made from Weber grill cooking grates.

The Polish Museum of America (984 N. Milwaukee Ave.) tells the story of Polish immigration to the new world, and to Chicago in particular, said to be the home of the largest Polish population in the world outside of Warsaw.

The National Italian American Sports Hall of Fame (1431 W. Taylor St.) pays tribute to those Italian Americans making their mark in the world of sports. Inductees include the obvious, like Phil Rizutto and Rocky Marciano, but also some surprises such as Mary Lou Retton and Phil Mickelson.

The International Museum of Surgical Science (1524 N. Lake Shore Dr.) is housed in a landmark lakeside mansion constructed by one of the heirs to the Diamond Match Company fortune. The museum, which launched in 1954, features more than 10,000 display items and traces the art and science of surgery from its primitive beginnings to present day.

The long-closed Castle Car Wash (3801 W. Ogden Ave.), in the North Lawndale section of town, was an early automotive business (1925) that resembles a crenellated medieval castle.

Greater Chicago

Nearby Oak Park is the home of the Frank Lloyd Wright Home and Studio (951 Chicago Ave.). Oak Park features more than twenty of Wright’s designs and, of course, tours are available.

Oak Park was also the boyhood home of Ernest Hemingway. The Ernest Hemingway Foundation of Oak Park includes the famous author’s birthplace (339 N. Oak Park Ave.) and a museum (200 N. Oak Park Ave.) containing first editions and Hemingway’s diary. Visitors are encouraged to begin their tour at the museum; Hemingway’s birth home is just a short walk away.

Within Greater Chicago is Des Plaines, home of the first franchised McDonald’s restaurant. (The very first McDonald’s, run by the McDonald brothers themselves, was in San Bernardino, California.) This was the first one run by Ray Kroc, a former salesman who liked the McDonalds’ concept and bought them out. Closed in 1983, it reopened a couple of years later as the McDonald’s Museum (400 N. Lee St.). Of course, McDonald’s is the organization which started the demise of so many mom-and-pop enterprises, and so is actually antithetical to Route 66.

In the community of Niles is the Leaning Tower of Niles (6300 W. Touhy Ave.), a half-size replica of the world-famous Leaning Tower of Pisa. It was constructed in the 1930s, and is located on the grounds of the local YMCA.


Route 66 begins in downtown Chicago, by the shore of Lake Michigan. This end of Route 66 presents an immediate challenge, since eastbound and westbound lanes are actually on separate streets. Westbound 66 follows Adams Street, while eastbound 66 is a block to the south, on Jackson. Since you don’t want to miss a thing, I suggest you drive on both streets to find as much of the old highway’s flavor as possible prior to leaving downtown.

Some of that flavor is to be found at Lou Mitchell’s Restaurant (565 W. Jackson Blvd.), a downtown Chicago eatery established in 1923, with its name spelled out in neon. It’s on eastbound 66 (westbound travelers can turn left off of Adams at DesPlaines, then turn left again onto Jackson). Don’t stop at Lou’s if you’re on a diet—patrons munch on free Milk Duds while waiting to be seated.

The easternmost end of Adams Street has as its landmark, the Art Institute of Chicago (111 S. Michigan Ave.), where countless American artists have received formal training. The Art Institute includes such famous works in its collection as Edward Hopper’s Nighthawks and Grant Wood’s American Gothic.

>> When you’re ready to leave Chicago and Lake Michigan, begin your adventure by proceeding west on Adams Street. Like all of the larger cities on Route 66, Chicago itself will not reveal much in the way of that Mother Road feel you are looking for—at least not when compared with the hundreds of smaller towns ahead of you. Cities like this were plotted out in the days well before automobile travel, so you and your car do not feel entirely welcome here.

Westbound Route 66 angles left (southwest) at Ogden Avenue, which is named for Chicago’s first mayor, William B. Ogden. He took office in 1837, at the time the city was first incorporated.

Continuing on Ogden, you will pass through the communities of Cicero and Berwyn.




Here in Cicero once stood a large muffler man figure holding a hot dog in front of Bunyon’s. He ws relocated to Atlanta, Illinois year ago, but there’s still Henry’s Drive-In, with a sign featuring a hot dog with fries.

There’s not a great deal that differentiates Berwyn—it’s suburban Chicago. But do check out Berwyn’s Toys & Trains (7025 Ogden Ave.).

Berwyn is also home to a Route 66 Museum (7003 W. Ogden Ave.) that will help you kick off your Mother Road journey. There’s even an electric-vehicle charging station right out front.


As you cross Centinela Boulevard on Route 66 (Santa Monica Boulevard), you enter the city of Santa Monica. Santa Monica Boulevard—and your run to the coast—abruptly ends at Ocean Avenue (although Route 66 actually turned left at Lincoln Boulevard and terminated at Olympic). Across Ocean Avenue is Pacific Palisades Park, where you should stroll around and relax now that you’ve come to the end of your journey. There is a small monument in the park dedicated to Will Rogers, which reads in part: “Highway 66 was the first road he traveled in a career that led him straight to the hearts of his countrymen.”

Popularly considered the symbolic end of Route 66, but technically blocks away, is the Santa Monica Pier, originally constructed in 1908. This may well be because the pier, with its large neon sign, is more photogenic than the true terminus on the nearby street corner. In keeping with the location’s status as the spiritual end of Route 66, a marker was dedicated in 2009 designating it as such. In the 1920s, Santa Monica had several recreational piers along its beach. This one was at one time called Ocean Park Pier, and when it reopened in 1958 as Pacific Ocean Park, there were more opening-week visitors than there had been at the grand opening of Disneyland three years earlier. Today, the pier includes a nine-story Ferris wheel, a five-story roller coaster, other rides, and midway-style games. Also here is the venerable Looff Hippodrome, named for carousel builder Charles Looff. Since 1916, the building has housed a hand-carved carousel. The one residing here currently is a 1922 model, which was brought here in 1946. The carousel was featured prominently in the 1973 movie The Sting, starring Robert Redford and Paul Newman, and was refurbished in 1981. The pier, much like Venice Beach to the south, is always awash with colorful local characters.



Santa Monica Attractions

Overlooking Santa Monica Canyon is the former home of composer Ferde Grofé (710 Adelaide Pl.). It was here that he composed his most famous work, the Grand Canyon Suite. The piece was originally titled Santa Monica Canyon Suite, but, fearing a lack of recognition, Grofé re-named it after the far more famous landmark. Grofé is also the man who wrote the world-famous orchestral arrangement of Gershwin’s Rhapsody in Blue. Gershwin had written the piece, not for symphony, but for a small band, with blank spaces left in it for Gershwin’s own piano improvisations. Grofé was at that time the chief arranger for the Paul Whiteman jazz ensemble, for whom the piece was originally written. Whiteman’s famous band was also where a crooner named Bing Crosby spent his salad days as one of the “Rhythm Boys.”

The Museum of Flying (3100 Airport Ave.) features more than thirty vintage aircraft, some of which are in flight-worthy condition, all maintained on the site where Mr. Donald Douglas built the very first DC-3.

Bergamot Station (2525 Michigan Ave.) is a collection of over twenty galleries housed in renovated warehouse spaces on approximately six acres in Santa Monica. Pieces include photography, paintings, sculpture, and more.

There’s a building in Santa Monica that may look vaguely familiar. The Santa Monica Civic Auditorium (1855 Main St.) was the regular site of the Academy Awards from 1961 to 1968.

The Galley restaurant (2442 Main St.) opened in 1934 and was popular with the likes of Errol Flynn. The restaurant has a seagoing theme, and features memorabilia from the 1935 film classic Mutiny on the Bounty.

Shirley Temple’s childhood home (924 24th St.) is also in Santa Monica.

The former City Hall (1438 2nd St.), constructed in 1873, is the oldest building of masonry construction in the city, and was designated a historical landmark in 1975.

The Annenberg Beach House (415 Pacific Coast Hwy) is a city-run public facility on five oceanfront acres. The facility is part of an estate originally developed by William Randolph Hearst in the 1920s, and it includes the rehabilitated guest house and pool, as well as new structures added during its conversion to public use.

The City of Santa Monica has prepared a “landmarks” tour brochure that includes a wealth of architectural sites of interest, including the Merle Norman Building (9130 Bellanca Ave.), the Vanity Fair Apartments (822 3rd St.), the Mayfair Theatre (214 Santa Monica Blvd.), and the Grofé residence cited above (710 Adelaide Pl.). Two-hour guided downtown walking tours are also conducted every Saturday morning at 10:00 am, beginning at the Hostelling International facility (1436 2nd St.).

Standing on the grounds of the Miramar Hotel (101 Wilshire Blvd.) is a century-old Moreton Bay fig tree with a story. It’s said that around 1890 or so there was a sailor in town with no money to pay his bar bill, so he paid the bartender with a young sapling instead. The sapling changed hands a couple of times, and then was eventually planted by the gardener of the Miramar estate, which stood where the hotel is now. The tree now stands about eighty feet tall near the corner of Wilshire Boulevard and Ocean Avenue.

Further Afield

Just northwest of Santa Monica is the Santa Monica Mountains National Recreation Area, bounded by the Pacific Ocean to the south and U.S. 101 to the north. Included within this preserve is the Will Rogers State Historic Park (1501 Will Rogers State Park Rd.), which includes the home Rogers lived in from 1928 until his death seven years later. There is also a visitor center, nature center, corral, stable, polo field, and hiking trails on the grounds. Adventurous hikers and bikers can take the Backbone Trail into the Santa Monica Mountains. The trail goes all the way to Point Mugu, some seventy miles away.

South of Santa Monica is Venice Beach. This area is prime habitat for surfers, down-and-outers, muscle builders, skateboarders, and an abundance of other species. Venice was the brainchild of one Abbot Kinney, who envisioned cloning Venice, Italy, right here in Southern California. Canals were dug throughout the area from 1904 to 1905, and two dozen black, silver-prowed gondolas were imported from Italy to ply the waters here. A tourist in 1906 observed: “The architecture was the grandest, an intricate blend of Italian columns, porticoes, and balustrades, only slightly marred by the presence of guess-your-weight machines.” At some point, the Board of Health declared the canals a health hazard and ordered that they be filled in. In the 1950s, Venice had deteriorated to the point that Orson Welles used the area as the backdrop for the film A Touch of Evil.

Of course we have only touched on part of the incredible journey on Route 66. Take a trip that will change your life.

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