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Get Your Kicks on Route 66: A Quirky Tour of Main Street U.S.A.

Written by Chris Caggiano

Embarking on a journey along Route 66 is like traveling through a living museum of American history and culture. This iconic highway, stretching from Chicago to Santa Monica, has captured the imagination of travelers for decades. Once a vital artery connecting the rural Midwest to the Pacific coast, Route 66 played a pivotal role in the country’s development, fostering trade and providing a lifeline to communities along its path.

With the advent of the interstate highway system, this once-bustling road fell into the shadows, giving way to faster, more direct routes. However, its charm and significance didn’t fade. Today, a drive along Route 66 represents a nostalgic trip back in time, offering a glimpse into the America of yesteryear. From the neon-lit motels and quirky roadside attractions to the small towns that hold the memories of a bygone era, it’s a road that tells a million stories.

Illinois

In Illinois, Route 66 begins its epic journey, offering travelers a taste of history and nostalgia. The adventure starts in Chicago at Lou Mitchell’s, an iconic diner and a Route 66 institution since 1923. Known as the “first stop on the Mother Road,” this diner welcomes road trippers with its famous complimentary donut holes and Milk Duds, a tradition that harks back to the diner’s early days.

As you venture out of the urban sprawl, Route 66 takes you to a more whimsical landmark in Collinsville: the World’s Largest Catsup Bottle. This 170-foot-tall water tower, built in 1949, was originally constructed for the G.S. Suppiger catsup bottling plant, which bottled Brooks old original rich & tangy catsup. This quirky structure is not only a beloved roadside attraction but also a symbol of America’s post-war optimism and love for novelty.

Missouri

As Route 66 winds through Missouri, it brings with it a mix of nostalgic charm and unique experiences. One notable stop is the 66 Drive-In in Carthage, a throwback to the golden age of American car culture. Established in the 1950s and restored in 1998, this drive-in is one of a handful remaining in the country, offering a chance to relive the classic American pastime of watching movies under the stars, just as travelers did in the heyday of Route 66.

Another must-visit is the whimsical Uranus Fudge Factory in Uranus, Missouri. More than just a fudge shop, this quirky destination embodies the roadside humor that Route 66 is famous for. (I mean, we don’t really need to explain it, do we?) It’s a place where fun and laughter are as plentiful as the sweet treats on offer. The Uranus Fudge Factory is a recent addition to the Route 66 landscape, yet it captures the spirit of the road perfectly — a little eccentric, always memorable, and undeniably fun.

Oklahoma

In Oklahoma, Route 66’s legacy continues with a blend of cultural depth and whimsical charm. A key highlight is the National Cowboy & Western Heritage Museum in Oklahoma City. Founded in 1955, this museum offers an immersive dive into the history of the American West. It houses an extensive collection of Western art, artifacts, and exhibits that celebrate the enduring spirit of the cowboy culture, a fundamental aspect of America’s heritage.

Another iconic stop in Oklahoma is Pops 66 Soda Ranch, a diner in Arcadia. Known for its striking 66-foot-tall soda bottle sculpture, Pops is a modern marvel of Route 66. Opened in 2007, the sculpture is a glowing beacon at night and a vivid landmark by day. Inside, the diner boasts an astonishing selection of over 700 soda flavors, making it a paradise for soft drink enthusiasts. Pops perfectly encapsulates the Route 66 spirit — innovative, fun, and always surprising, offering a refreshing break in the journey through the Sooner State.

Texas

The leaning tower of texas

The Leaning Tower of Texas, Britten, TX

In Texas, Route 66 travelers encounter landmarks that are as unique as they are iconic. A quintessential stop is Cadillac Ranch, located just west of Amarillo. Created in 1974 by a group of artists known as The Ant Farm, this public art installation features ten Cadillac cars half-buried nose-first in the ground, aligned in a row. Over the years, these cars have become a canvas for visitors to leave their mark with spray paint, continually transforming the installation into a vibrant and colorful display of public art.

Another fascinating stop in the Texas stretch of Route 66 is the Leaning Tower of Texas in Groom. This deliberately tilted water tower, designed to catch the eye of passersby, has become an amusing photo opportunity for travelers. While it was originally constructed as a gimmick by a local truck stop, the Leaning Tower has since become an emblematic part of the Route 66 landscape in Texas.

New Mexico

Spiral staircase in Loretto Chapel, Santa Fe. New Mexico

Spiral staircase, Loretto Chapel, Santa Fe. New Mexico

In New Mexico, Route 66 traverses landscapes filled with cultural richness and historical intrigue. The Loretto Chapel in Santa Fe stands out as a must-visit destination. This chapel, famous for its “miraculous” spiral staircase, was built in the late 19th century. The staircase is renowned for its remarkable design – with no visible means of support and a mysterious history regarding its construction. The Loretto Chapel embodies the blend of Spanish and indigenous influences that characterize New Mexico’s unique architectural and cultural heritage.

Another gem along Route 66 in New Mexico is Canyon Road in Santa Fe. This historic area is a vibrant artery of the art scene, home to over a hundred galleries, studios, and boutiques. Here, visitors can explore a wide range of art, from traditional Native American pieces to contemporary works. The road itself, with its adobe buildings and picturesque settings, offers a glimpse into the artistic soul of the Southwest.

Arizona

A view of the old semi-ghost town Jerome in Northern Arizona

Ghost town, Jerome, Arizona

As Route 66 winds through Arizona, it showcases a blend of historical intrigue and vibrant culture. One noteworthy stop is Jerome, Arizona. Once a thriving copper mining town, Jerome transformed into a ghost town after the mines closed. Today, it has been reborn as a vibrant arts community, with its historic buildings hosting galleries, shops, and cafes. This hillside town, clinging to the Cleopatra Hill, offers stunning views and a fascinating glimpse into Arizona’s mining past.

Another must-visit location in Arizona is MartAnne’s Breakfast Palace in Flagstaff. Celebrated for its delicious Southwestern cuisine, MartAnne’s serves up hearty dishes that reflect the rich culinary traditions of the region. It’s a favorite among locals and travelers alike, making it a perfect stop for those looking to experience the authentic flavors of Arizona.

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California

Art installation with collected beer bottle at Elmer's Bottle Tree Ranch, San Bernardino, California.

Elmer’s Bottle Tree Ranch, Oro Grande, California

In California, the final chapter of the Route 66 journey unfolds with unique and memorable experiences. First, travelers encounter the whimsical Bottle Tree Ranch in Oro Grande. Created by Elmer Long, this enchanting outdoor gallery features a collection of metal “trees,” each adorned with colorful glass bottles and various found objects. This artistic haven in the Mojave Desert offers a magical and surreal experience, showcasing the imaginative spirit of Route 66.

As the journey nears its end in Los Angeles, the route leads to Muscle Beach in Venice. Known as the legendary outdoor gym, Muscle Beach has been a hub for bodybuilding enthusiasts since the 1930s and epitomizes the vibrant beach culture of Southern California. Here, visitors can witness or partake in outdoor workouts against a backdrop of ocean views, experiencing a slice of the iconic Californian lifestyle.

FAQs: 

Q: What is the best time of year to travel Route 66?
A: The ideal time to travel Route 66 is from late spring to early fall, particularly between May and October. During these months, the weather is generally more favorable for road trips, with fewer chances of extreme conditions that can occur in winter or mid-summer.

Q: Are there guided tours available for Route 66?
A: Yes, there are several companies that offer guided tours of Route 66. These tours can range from self-guided itineraries to fully escorted trips with a guide. They often include key attractions along the route and can be a great option for those who prefer structured travel.

Q: What kind of accommodation options are available along Route 66?
A: Accommodations along Route 66 vary widely, from classic motels and RV parks to boutique hotels and bed-and-breakfasts. Many travelers opt for the historic motels for an authentic experience.

Q: Is Route 66 suitable for motorcycle travel?
A: Absolutely, Route 66 is a popular route for motorcycle enthusiasts. The road offers a diverse range of landscapes and is well-suited for bikers. However, it’s important to plan ahead for fuel stops and accommodations, as some sections of the road are less populated.

Q: How long does it typically take to drive the entire length of Route 66?
A: The duration of a Route 66 road trip can vary greatly, but on average, it takes about two to three weeks to comfortably travel the entire length of Route 66, allowing time for sightseeing and stops along the way.

Q: Are there mobile apps or guides that can help navigate Route 66?
A: Yes, there are several mobile apps and guidebooks available that provide detailed information on Route 66 attractions, history, and navigation. These resources can be invaluable for planning your trip and ensuring you don’t miss any hidden gems.

Q: Can I still find original sections of Route 66 to drive on?
A: Yes, there are many original sections of Route 66 still accessible for driving. However, since Route 66 was decommissioned as a U.S. Highway, some parts have been replaced by the Interstate Highway System. Maps and guides can help you locate these historic stretches.

Did we miss your favorite stop along Route 66? Tell us about it in the comments below! 

About the author

Chris Caggiano

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