16 Days /15 Nights  Gateways:  Chicago & Los Angeles

1 & 2: Chicago

Welcome to Chicago!  Check into your hotel, and begin your exploration.  You’ll find magic in sparkling Chicago, attractions like Navy Pier – the Midwest’s top tourist destination – and its boardwalk, Ferris wheel, boat tours, and countless dining or shopping options. Millennium Park offers dazzling music, art, landscape design and architecture – including the mammoth stainless-steel Cloud Gate sculpture. Chicago looks great from every angle, whether you’re exploring the city’s astonishing architecture during a guided tour (on foot or aboard a Chicago River boat, lakeshore cruise or sightseeing bus) or you’re enjoying the birds-eye view from the 103rd floor Sears Tower Skydeck and the 94th floor Hancock Observatory. The city’s 29 miles of lakefront paths are just one reason Chicago is one of the world’s most walkable and beautiful cities

2 Nights Chicago, IL

3: Springfield, IL (208 mi/344 km)

Start your road trip with breakfast at Lou Mitchell’s in downtown Chicago, a fixture on Route 66 since 1923. Then head to Jackson Boulevard at Lake Shore Drive, considered the official start of Route 66. Drive out to suburban Joliet and stop at the Route 66 Welcome Center in the Joliet Area Historical Museum. Lunch at Dell Rhea’s Chicken Basket in Willowbrook, a Route 66 favorite since the 1940s. Head to Wilmington to see the famed Gemini Giant, a 28-foot-tall spaceman in front of the Launching Pad Drive-In. Motor over to the historically preserved Odell Station. Next stop is the Dixie Trucker’s Home in McLean, an expansive restaurant and gas station that houses the Route 66 Association of Illinois Hall of Fame. And don’t forget a bite at Springfield’s nostalgic Cozy Dog Drive-In. Stop at Shea’s Gas Station Museum in Springfield to hear stories from Route 66 business owner Bill Shea.

1 Night Springfield, IL

4: Springfield, MO (313 mi/521 km)

Have lunch in Litchfield at the Ariston Cafe, still decorated with 1920s furnishings. Henry’s Rabbit Ranch in Staunton celebrates Route 66 with memorabilia displayed in a replica vintage gas station. See the Old Chain of Rocks Bridge in Madison, built in 1929 to span the Mississippi River and now the largest pedestrian bridge in the world.

1 Night Springfield, MO

5: Oklahoma City, OK (283 mi/472 km)

The Ozark Highlands of southern Missouri, which Route 66 crosses in its 300-odd-mile journey between Illinois and Kansas, are about the only significant hills the road crosses east of Arizona. This plateau region, though not by any means alpine or breathtaking, is visually dynamic in a way the broad flatlands of Illinois and the Great Plains rarely are. Though the I-44 freeway has replaced the old road all the way across the state, many signs of the old highway line the surviving stretches of the original route, and every exit drops you within a moment’s drive of the Mother Road. Missouri also holds one of the greatest of the old Route 66 tourist attractions—Meramec Caverns, an extensive set of limestone caves offering the most over-the-top underground tour you can take. The shortest but perhaps best-signed stretch of Route 66’s eight-state run is its 14-mile slice across the southeast corner of Kansas.

1 night Oklahoma City

6: Amarillo, TX (263 mi/440 km)

Travel today to Amarillo. Apart from occasional college football teams, Oklahoma doesn’t often get to crow about being the best in the country, but as far as Route 66 is concerned, the state is definitely number one. Containing more still-drivable miles of the old highway than any other state, this is definitely Mecca for old-roads fans.   Known as the Panhandle because of the way it juts north from the rest of Texas, this part of the route is a nearly 200-mile stretch of pancake-flat plains.  The commercial center of the Texas Panhandle, Amarillo arose when the Fort Worth and Denver City Railway started laying track in the area in 1887, a decade after ranchers began to graze their cattle on the buffalo grass-speckled plains. When the town was formally incorporated, the name Amarillo — meaning “yellow” literally and “wild horse” figuratively — was adopted from a nearby lake. In a little over a decade, the combination of the railroad and the ranchland led to the establishment of Amarillo’s long-standing status as a cattle-shipping capital. To this day, the city “smells like money!”

1 night Amarillo, TX

7 & 8: Albuquerque, NM (287 mi/480 km)

Old Route 66 has been replaced by I-40 most of the way across Texas, though in the sole city, Amarillo, old US-66 survives as the main business strip, lined by the remains of roadside businesses. Following old Route 66 across New Mexico gives you a great taste of the Land of Enchantment, as the state calls itself on its license plates. The many towns and ghost towns along I-40, built more or less on top of Route 66, still stand. In Albuquerque, Route 66 runs through the center of this sprawling Sun Belt city.

2 nights Albuquerque, NM

9: Flagstaff, AZ (325 mi/541 km)

Western New Mexico has the most to see and the most interesting topography, with sandstone mesas looming in the foreground and high, pine-forested peaks rising in the distance. Paralleling the Santa Fe Railroad, the route passes through the heart of this region, and numerous detours—to Inscription Rock and Chaco Canyon, among others make unforgettable stops along the way. At the New Mexico border, Arizona welcomes west-bound travelers with an overwhelming display of trading-post tackiness. The gift shops themselves may not be all that attractive, but the old Route 66 frontage road along here and east into New Mexico is truly spectacular, running at the foot of red-rock cliffs.  One place that’s worth a stop here is Petrified Forest National Park.  Just east of Flagstaff is the most easily accessible of the hundreds of different prehistoric settlements all over the southwestern United States, Walnut Canyon National Monument.

1 Night Flagstaff, AZ

10 & 11: Grand Canyon, AZ (73 mi/121 km)

From the east end of Williams, Hwy-64 continues 60 miles due north to one of the wonders of the natural world, the Grand Canyon of the Colorado River. Two hundred miles long, a mile deep, and anywhere from 5 to 15 miles across, the Grand Canyon defies description, and if you’re anywhere nearby you owe it to yourself to stop for a look. You could spend a lifetime here and still not get to know it all, but even if you have only half a day be sure to leave the rim and hike down into the canyon to get a real sense of its awesome scale.

2 Nights Grand Canyon

12: Needles, CA (238 mi/398 km)

Probably the most evocative stretch of old Route 66 runs northeast from Seligman to Kingman through the high-desert Hualapai Valley, along the Santa Fe Railroad tracks through all-but-abandoned towns bypassed by the “modern” Interstate world. You will enter Hualapai Reservation lands. The 700-strong tribe has its community center at the town of Peach Springs, which marks the halfway point of this 90-mile, old-roads loop and offers at least one reason to stop:  “River Runners’” restaurant, right on Route 66. Peach Springs is mostly a prefab housing project with few services, though there is a photogenic old Route 66 filling station at the center of town. Another 10 miles west brings you to the town of Truxton, where the Frontier Cafe is the one reliable place to eat in this sparsely populated region—good pie and great chat, open daily. Then it’s on across a small section of the Hualapai Indian Reservation, centered around the village of Valentine. There’s a 20-mile-long straightaway, the road (now named Hwy-66) around the Peacock Mountains through the old railroad town of Hackberry, to Kingman. The only town for miles in any direction since its founding as a railroad center in 1880, Kingman (pop. 20,069) has always depended upon passing travelers for its livelihood. Long a main stopping place on Route 66, and still providing the only all-night services on US-93 between Las Vegas and Phoenix, and along I-40 between Flagstaff and Needles, the town remains more a way station than a destination despite the increasing number of people who have relocated here in recent years, attracted by the open space, high desert air, and low cost of living. Continue through Lake Havasu City, where you’ll find the London Bridge, to Needles, CA for overnight.

1 night Needles, CA

13, 14 & 15: Los Angeles (260 mi/434 km)

End your holiday with a three night stay in Los Angeles. Tour Hollywood, see the stars on the sidewalks; Disneyland and Knott’s Berry Farm, and eat dim sum in Chinatown.  Visit Universal Studios, where the shows and rides are so much fun.

3 nights Los Angeles, CA

16: Homeward Journey

At the end of your stay, return your rental car to and begin your homeward journey.

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