Getting Our Kicks on 66: A Photo Gallery of the Route’s Historic Landmarks Then and Now

The 2,448-mile “Mother Road” connecting Chicago to Santa Monica once served as America’s main street. Route 66 created its own culture of quirky roadside attractions, classic diners, and unforgettable landmarks. While the highway was officially removed from the US Highway System in 1985, many of its iconic stops remain. Let’s explore how these beloved landmarks have changed over the decades.

The Gateway Arch

While not directly on Route 66, St. Louis’s magnificent arch stands close enough to the route to have become associated with Mother Road journeys. Completed in 1965, the 630‑foot stainless steel monument transformed the St. Louis riverfront and created an iconic symbol of westward expansion. Today’s arch looks remarkably unchanged, though its surroundings have been completely redesigned with an expanded museum beneath the structure and better integration with downtown St. Louis through the new Gateway Arch National Park.

Barstow Harvey House

Once the crown jewel in Fred Harvey’s railway dining empire, this Spanish-Renaissance station and hotel hosted weary rail passengers before becoming a Route 66 icon. In its heyday, immaculately dressed “Harvey Girls” served quality meals to travelers in elegant surroundings. After decades of decline following reductions in passenger rail service, the building now houses the Route 66 Mother Road Museum and Barstow’s Amtrak station, preserving its stunning architecture while telling the story of America’s transportation evolution.

Cadillac Ranch

In 1974, eccentric millionaire Stanley Marsh 3 commissioned the art group Ant Farm to create this striking installation of ten Cadillacs half-buried nose-down in a Texas field. Originally featuring cars from 1949–1963 in pristine condition, the installation has transformed over the decades as visitors added their own touches. Today, the cars are barely recognizable under countless layers of spray paint, yet they remain one of Route 66’s most photographed attractions, proving that sometimes change becomes part of the charm.

Meramec Caverns

Advertised on barn roofs and birdhouses for hundreds of miles, these limestone caves became one of Route 66’s must-stop attractions under the promotional genius of owner Lester Dill. Once promoted as Jesse James’ hideout, the caverns featured theatrical lighting and guided tours that turned natural formations into entertainment. Today, while the famous “Stage Curtain” formation still illuminates in patriotic colors, modern environmental concerns have led to more educational approaches about cave conservation alongside the classic roadside appeal.

Old Trails Bridge

This historic steel truss bridge spanning the Colorado River connected Arizona and California when Route 66 was in its prime. Built in 1916 as part of the National Old Trails Road, it carried westbound travelers on their final stretch toward the Pacific. Though replaced for automotive traffic by newer spans, the bridge still stands alongside I-40, now carrying a pipeline. Its distinctive red trusses remain a powerful reminder of the engineering that first made cross-country travel possible.

Arcadia Round Barn

Built in 1898 by local farmer William Odor, this perfectly round wooden barn became an instant Route 66 landmark when the highway was established. The unique structure, with its circular design and domed roof, attracted travelers for decades before falling into disrepair in the 1970s. Today, thanks to extensive restoration efforts completed in 1992, the Round Barn stands proudly again, serving as a museum and event space that draws tourists seeking authentic Route 66 experiences.

Santa Monica Pier

The western terminus of Route 66 provided the reward of Pacific Ocean views after more than 2,000 miles of driving. The pier’s carousel, arcade, and other amusements welcomed tired travelers who had finally reached the end of their journey. Today’s pier retains its classic charm while adding modern attractions. The official “End of the Trail” sign creates the perfect photo opportunity for Route 66 enthusiasts who complete the historic journey, even though they likely traveled on interstates for much of their trip.

The Blue Whale of Catoosa

Hugh Davis built this smiling cement whale in the early 1970s as an anniversary gift for his wife, who collected whale figurines. The 80‑foot blue whale quickly became a beloved swimming hole and picnic spot for Route 66 travelers. After falling into disrepair following the Davis family’s retirement, local volunteers restored the grinning giant. Today, while swimming is no longer permitted, the Blue Whale remains a cherished photo opportunity and a quirky reminder of Route 66’s playful spirit.

Roy’s Motel and Cafe

The futuristic neon sign and striking triangular roofline of Roy’s became an essential beacon in the Mojave Desert for Route 66 travelers. Opened in 1938 by Roy Crawl as a gas station, it expanded to include a cafe and motel featuring distinctive mid-century modern architecture. After decades of decline following interstate construction, Roy’s has recently experienced revitalization. While the cafe no longer serves meals, the restored neon and repainted cabins continue attracting photographers and nostalgia seekers to Amboy, California.

The Painted Desert

Nature’s own roadside attraction, the Painted Desert’s striated badlands showcased spectacular color variations that seemed almost artificial to first-time visitors. Route 66 travelers would pull over at overlooks to marvel at the pink, red, and purple sedimentary layers. Today, while the natural wonder remains essentially unchanged, improved facilities at Petrified Forest National Park provide better interpretation of the geological processes that created this stunning landscape, helping visitors appreciate not just its beauty but its scientific significance.

The Route 66 Drive-In Theatre

Outdoor movies under the stars represented classic Americana during Route 66’s heyday, with drive-ins dotting the entire route. These family-friendly venues combined America’s love for automobiles and cinema. While most drive-ins closed as land values increased and home entertainment options expanded, some have experienced remarkable comebacks. Restored drive-ins along the old route now offer nostalgic movie experiences alongside modern films, proving that some mid-century pleasures remain irresistible even in the digital age.

Wigwam Hotel

“Sleep in a Wigwam!” promised the signs for these concrete teepee-shaped motel rooms built in the 1930s–40s. Originally part of a chain, the surviving locations in Holbrook, Arizona and San Bernardino, California became iconic Route 66 experiences. Despite their culturally insensitive confusion between wigwams and teepees, these quirky accommodations have been lovingly preserved. Modern travelers can still spend the night in these Instagram-worthy concrete cones, now equipped with air conditioning and other contemporary amenities while maintaining their vintage exterior charm.