From giant green dinosaurs in Holbrook, AZ, and a 170-foot Catsup bottle-shaped water tower in Oklahoma City to kitschy general stores and vintage diners, Route 66 has quirky landmarks and peculiar roadside attractions that make taking a break well worth the trip.

Image courtesy of worldslargestcatsupbotttle.com

Image courtesy of route66roadtrip.com, via roadtravelamerica.com

AAA projects 73 million Americans will travel by car this Thanksgiving week, an additional 1.3 million people on the road compared to last year. Between flight cancellations, FAA staffing shortages and long lines at TSA, AAA warns “that number could end up being higher if some air travelers decide to drive instead of fly” (newsroom.aaa.com).

So if you hit the road this holiday, you should drive the most famous, Route 66. Established in 1926 and stretching 2,448 miles, it was intended to connect rural communities in the Midwest to the West, passing through Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona and California. Coined “The Mother Road” by John Steinbeck in his 1939 novel “The Grapes of Wrath,” it was the primary route for migrant workers during the Dust Bowl era. Also known as the Main Street of America, truckers used the zigzagging route to transport grain and produce through the prairie lands, linking small Midwest farming towns with West Coast markets (route66roadtrip.com). With the popularity of automobiles, gas stations, restaurants, and souvenir shops sprung up along the route. The legendary highway has been immortalized in songs, movies and books. While you no longer can drive the original route, preserved portions of Route 66 boast historical sites and architectural landmarks.

Gateway Arch, St. Louis, MO

The Gateway Arch, commemorating America’s westward expansion, is the tallest monument in the US standing at 630 feet. Designed by famed architect Eero Saarinen, its complex and subtle architectural curve had never been attempted on such a large scale and is now a landmark in St. Louis. Take the Tram Ride to the top for unbeatable views.

Pops66, Arcadia, OK

Image courtesy of pops66.com

Lit up in LED lights, a 66-foot-tall bottle of pop is an ode to, as the name suggests, soda pop. Featuring a restaurant, gas station and convenience store, the Googie-inspired ultramodern design boasts a dynamic cantilever roof (randelloittarchitects.com). With tons of bubbly drinks in every color and (wacky) flavor imaginable, this must-see stop is a monument to “fuel and fizz” that harks back to the glory days of the open road.

The Round Bar, Arcadia, OK

*Image courtesy of arcardiaroundbarn.com*

Measuring 60 feet in diameter and 43 feet tall, the Round Barn was built in 1898 “using native bur oak boards soaked … and forced into the curves needed for the walls and roof rafters” (arcadiaroundbarn.com). An unusual shape for a barn, the farmer figured tornadoes would “hit and go around it instead of through it.” (According to the website, there is no scientific evidence to support this theory.) Today the barn hosts public tours, live music and events.

Conoco Tower Station and U-Drop Inn Café, Shamrock, TX

The Tower Station and Café look much like they did when they were built in 1936. Featuring Art Deco detailing, two towers and topped with a metal tulip, it “is one of the most imposing and architecturally creative buildings along the … road” (nps.gov). It was used as the model for Ramone’s Body Art in the movies Cars and Cars II.

San Miguel Chapel, Santa Fe, NM

*Image by Carla D. Abeyta, via sanmiguelchapel.com*

Referred to as the oldest church in the continental United States according to oral history, the adobe chapel served a small community of soldiers, laborers and Native Americans. Partially destroyed during the Pueblo Revolt of 1680, the present building dates from 1710 and has undergone several restorations to preserve one of the best examples of adobe architecture. It has served as a place of worship, an infirmary, military chapel, and venue for concerts and ceremonies.

KiMo Theatre, Albuquerque, NM

Built in 1927 the KiMo theater’s unique Pueblo Deco design blends indigenous Pueblo motifs with Art Deco elements, reflecting the city’s rich cultural heritage (cabq.gov). Constructed in the palatial style typical of theaters during this time, the brown stucco exterior was embellished with southwestern ornamental details in glazed terra cotta tiles and vividly colored reliefs. The building is topped with a frieze of Hopi sun shields, Puebloan rain motifs and Navajo symbols. “The interior was designed to look like the inside of a ceremonial kiva, [a sacred room traditionally used by Pueblo people], with log-like ceiling beams painted with dance and hunting scenes” (nps.gov).

Standing on the Corner, Winslow, AZ

Image courtesy of standinonthecorener.org

SK’s Jessica Handy on site

Just as the Eagles sang, you’ll be “standing on the corner of Winslow, AZ” in this public park that boats a giant Arizona Route 66 emblem stamped onto the road. Today they hold an annual music festival on this spot.

Roy’s Motel & Cafe, Amboy, CA

A prime example of Googie architecture (neon, futuristic, geometric), Roy’s 50-foot neon Jetson-style sign beaconed travelers to the gas station, café and motel. Roy’s was a favorite stop enroute to Amboy’s volcanic crater a few miles away that still attracts visitors for star gazing into the surrounding dark skies. Besides the gas station and gift shop, Amboy is literally a ghost town with a 2024 census showing a population of zero!

End of Route 66, Santa Monica, CA

The iconic route comes to a stop in Santa Monica. A symbolic sign commemorates the “End of the Trail” on the Santa Monica Pier while the real route ends by Mel’s Diner at the intersection of Lincoln and Olympic Blvd.

Ahead of the highway’s centennial festivities in 2026, Santa Monica Travel & Tourism kicked off a Route 66 Song Contest inviting musicians and songwriters to submit original songs celebrating the iconic highway’s ties to the city (https://www.santamonica.com/route66/).

While we are more architecturally than musically inclined, here’s a tried-and-true Route 66 Playlist:

Get Your Kicks on Route 66, Rolling Stones
Take it Easy, The Eagles
Highway 66 Blues, Woody Guthrie
Life is a Highway, Tom Cochrane
Route 66, Nat King Cole (also covered by Chuck Berry, among others)
Cadillac Ranch, Bruce Springsteen (references the half-buried Cadillacs covered in graffiti along the route in Amarillo, TX)
Amarillo by Morning, George Strait
Tucumcari Tonight, Brian Langlinais (a bluesy ode to a man getting home to this NM stop on the route)

Get Your Kicks On…