Route 66 Is Full of Design Landmarks—These Are the 14 You Can’t Miss

With stops at a Frank Lloyd Wright home and historic Art Deco buildings, plan an architecture-centered road trip to celebrate the Mother Road’s 100th anniversaryThe Eero Saarinen-designed Gateway Arch is just one stop on our design-filled road trip.Photo: Mark Perry/Getty ImagesRoute 66, or the Mother Road as John Steinbeck called it in The Grapes of Wrath, turns 100 this year. And while the centennial celebration is the perfect time to celebrate all things related to roadtrips—gas station snacks, carefully curated playlists, rearview mirror decor—it’s also a welcome call to hit the highway in search of some seriously dazzling architectural sights. Here, we’ve rounded up 14 can’t-miss design landmarks along Route 66, with a healthy dose of kitsch sprinkled throughout. Take a peek at Honest Abe’s former abode, walk one of the country’s most impressive Art Deco districts, take part in a hands-on art installation spray-painting Cadillacs in the middle of a field, and more. Consider the Mother Road a 2,400-mile design museum, from its start in Chicago to its end point in Santa Monica.1. The Art Institute of Chicago (Chicago, Illinois)The Art Institute of Chicago Photo: Barry Winiker/Getty ImagesKick off your trip with an architectural colossus—the Windy City, one of the most dynamic destinations in the country. The Art Institute of Chicago is a must-visit, with its greatest hits—including Grant Wood’s American Gothic, Edward Hopper’s Nighthawks, and Picasso’s The Old Guitarist—as well as a dedicated architecture and design department that has curated more than 250,000 objects dating as far back as the 1870s. But it’s not just the museum’s collection that’ll leave you slack-jawed. The building itself, especially the Renzo Piano–designed Modern Wing, is a sight to behold.Need to rest up before hitting the road? Pendry Chicago is an easy 10-minute walk to the Art Institute and is housed within the iconic 1929 Art Deco Carbide & Carbon Building. Map out your road trip over Campari cocktails and live music at Château Carbide (a.k.a. the hotel’s Speakeasy in the Sky), then wander out to the terrace to get a view of Chicago’s skyline, including the famed “corncob towers” (Marina City).2. Two Iconic American Homes (Springfield, Illinois)The Lincoln home Photo: Sean Pavone/Getty ImagesArchitecture lovers and history buffs will find common ground at the Lincoln Home, a National Historic Site. Take a tour of the 16th president’s former residence on Eighth and Jackson Streets, where he and his family lived for 17 years before he became president. The 25-minute tour includes a peek at the formal parlor, kitchen, dining room, and the family members’ bedrooms. Just down the road, you can visit Frank Lloyd Wright’s Dana-Thomas house, a Prairie-style masterpiece built in the early 1900s. While touring the 12,000-square-foot home, you’ll also be able to see more than 100 pieces of furniture and 450 art glass windows, doors, and light fixtures designed by the visionary.The Dana-Thomas house Photo: Buyenlarge/Getty ImagesWhile you’re in town, be sure to feed your appetite for Route 66 kitsch too. Springfield is home to the Cozy Dog Drive-In, which has been serving corn dogs since 1949, and Route 66 Motorheads—part bar and grill, part roadway museum, and part entertainment complex.3. Gateway Arch (St. Louis, Missouri)The Gateway Arch Photo: Mike Kline/Getty ImagesIf you know one thing about St Louis, it’s probably that it’s home to a massive stainless-steel arch. But what you might not know is that you can take a joy ride to the top of Eero Saarinen–designed 630-foot structure, known as the Gateway to the West, which also just so happens to be the world's tallest human-made arch. Futuristic five-person pods transport visitors to the top within minutes, and from its peak you can see up to 30 miles in either direction on a clear day. The full Gateway Arch experience takes roughly an hour, with the chance to peruse a historic exhibition and snap a souvenir photo in addition to the gravity-defying ride.4. Pythian Castle (Springfield, Missouri)Pythian Castle Photo: Miguel Angel Soto Lopez/Getty ImagesIn the birthplace of Route 66 (Springfield is where the highway got its name) stands Pythian Castle, a regal 1913 limestone structure with an intriguing yet non-royal past. Originally it served as an orphanage and later, after the military took it over, housed German and Italian prisoners of war during WWII. Today it’s an event space that’s open for history tours during the day and ghost tours at night—good news if you roll into town late and don’t mind potential encounters with the paranormal.5. Bonnie and Clyde’s Hideout (Joplin, Missouri)The apartment where Bonnie and Clyde hid from authorities Photo: Bill Chizek/Getty ImagesAdd an element of infamy to your trip (without earning an actual rap sheet) by bunking at Bonnie and Clyde’s former hideout. The garage apartment where the notorious outlaws holed up for nearly two weeks in 1933 before taking part in a shootout with law enforcement and skipping town is now a two-bed, two-bath Airbnb. Also in town, the Spiva Center for the Arts features works from locals, and the Route 66 Mural Park is a colorful ode to the Mother Road.6. Downtown Deco District (Tulsa, Oklahoma)Downtown Tulsa, Oklahoma Photo: Dee Liu/Getty ImagesMiami might get the lion’s share of Art Deco attention in the US, but don’t sleep on Tulsa. The city has a dedicated Deco District with dozens of buildings in the signature 1920s style. Pull up an online walking tour map, or swing by the Decopolis TulsaRama Town Square to get a paper copy, and take a DIY Deco tour to see iconic spots like the Philcade and Tulsa Club buildings.7. The Paseo Arts District (Oklahoma City, Oklahoma)Established in the 1920s, The Paseo is home to over 80 artists who show their work in some 20 galleries, many housed in Spanish revival buildings with their original stucco and clay-tile roofs intact. A super walkable slice of Oklahoma City, this is the place to appreciate art, pop into local boutiques, and grab a vegan donut.The Paseo Arts District Photo: Walter Bibikow/Getty ImagesIf you need a snooze at this point in your trip, you can’t go wrong with Bradford House, a member of Design Hotels. The heirloom-packed, color-saturated stay is spread across two buildings, one a historic home built in 1912. Owners Sara Kate Little and Jason Little personally picked most of the hotel’s antiques on trips throughout Europe and the US. A stay here will inspire you to do a little collecting on your own road trip.8. Cadillac Ranch (Amarillo, Texas)Cadillac Ranch Photo: Getty ImagesEverything’s bigger—and sometimes more bizarre—in the Lone Star State, where an Amarillo art installation invites visitors to spray-paint 10 half-buried Cadillacs in a field. Cadillac Ranch has been giving road-trippers an unexpected artistic experience since 1974. After leaving your mark, mosey over to The Big Texan, famous for its 72-ounce steak challenge—eat it all in one hour and it’s free.9. Murals of Tucumcari (Tucumcari, New Mexico)Murals of Tucumcari Photo: Teresa Otto/Getty ImagesIn eastern New Mexico, the tiny town of Tucumcari has a population of just over 5,000 people and an impressive collection of nearly 100 public murals. See Western landscapes, tributes to the Route 66 sign, and even portraits of Billy the Kid, Elvis, and James Dean on the sides of buildings.10. Santa Fe Plaza (Santa Fe, New Mexico)Adobe buildings in Santa Fe Photo: Getty ImagesFor more than 400 years, this plaza dotted with adobe buildings has been the cultural and economic center of New Mexico’s capital city. On the north side of the plaza, the Spanish-built Palace of the Governors dates back to 1610. Today, it’s home to the New Mexico History Museum and is a popular spot to pick up a unique souvenir—Native American artisans line the outdoor portal to sell handcrafted jewelry, pottery, and textiles daily. Elsewhere on the plaza, Shiprock Santa Fe offers a treasure trove of century-old Navajo rugs and concho belts, and La Plazuela is the place to indulge in cheese-stuffed hatch green chiles in a 1920s building. While in town, you can also visit the Georgia O'Keeffe museum for a dose of painted American modernism.11. The Petroglyphs at Petrified Forest National Park (Holbrook, Arizona)Petroglyphs at Petrified Forest National Park Photo: Edward Palm/Getty ImagesRoute 66 passes through only one national park, and it’s more than just a place to stretch your legs (though with over 220,000 acres, you’ll have ample opportunity to do that). Petrified Forest National Park is famous for its stone trees—200-million-year-old wood that has turned to crystal quartz—its rich concentration of plant and animal fossils, and its vibrantly colored badlands. But it’s also home to some 800 archaeological sites with structures built by ancestral Puebloan people as well as ancient rock carvings that date as far back as 2,000 years.12. Riordan Mansion State Historic Park (Flagstaff, Arizona)Riordan Mansion State Historic Park Photo: Faina Gurevich/Getty ImagesFans of Arts and Crafts–style architecture should hightail it to Flagstaff, where one of the country’s most exquisite examples is open to the public for tours. Riordan Mansion, built in 1904, was designed by Charles Whittlesey, who also did the Grand Canyon’s impressive El Tovar Hotel. In addition to getting a close-up of the 40-room home’s rustic log siding and stone arches, visitors also get an eyeful of craftsman furnishings, including original pieces by Gustav Stickley and Harvey Ellis.13. Harvey House Railroad Depot (Barstow, California)Harvey House Railroad Depot Photo: Benny Marty/Getty ImagesWith a pitstop at the Harvey House Railroad Depot, you’ll get a feel for both early-20th-century architecture and travel. Built between 1910 and 1913, the depot was part of a chain of railroad restaurants and hotels called Harvey Houses, each with a name reflective of its surroundings—this one was originally called Casa del Desierto (House of the Desert). Designed by Mary Colter, the building blends Spanish Renaissance and Southwest American Indian architecture, reflecting its Mojave Desert surroundings. Today, the depot is home to The Mother Road Museum, with exhibits dedicated to Route 66, making it doubly worth a visit.14. Santa Monica Pier (Santa Monica, California)Santa Monica Pier Photo: Mindaugas Dulinskas/Getty ImagesIt’s the endpoint to Route 66, a superb spot to snap a celebratory photo, and—despite what your LA friends may say—much more than a tourist trap. The Santa Monica Pier is an LA design landmark, combining structures built in 1909 and 1916. On it, the Looff Hippodrome, which houses a carousel featuring hand-carved animals and sleighs, also dates back to 1916. Blending Byzantine, Spanish, and Moorish elements, the whimsical building is the work of Charles I. Looff, who built the first carousel at Coney Island before his West Coast pursuits.For even more LA landmarks and a finale celebration fitting for a 2,400-mile journey, spend a few nights at the nearby Fairmont Miramar Hotel & Bungalows. The historic hotel—with origins as a 19th-century seaside estate that became a hotel in 1921 (Greta Garbo loved it so much she stayed for four years)—is offering a luxe Grand Finale package in honor of Route 66’s centennial. The offer includes two nights in a bungalow, a private helicopter experience, dinner aboard a yacht, and a tour of LA’s most iconic landmarks in a chauffeur-driven vintage car, since you’ll likely be tired of driving yourself.Not a subscriber? Join AD for print and digital access now.Sign up for our daily newsletter to get the best of design in your inbox.Amelia Mularz is a freelance journalist specializing in interior design, garden, and travel stories. She has previously contributed to Real Simple, HGTV Magazine, New York magazine's The Strategist, and Travel + Leisure, among other titles. She has also held long-term roles at Vogue and The Knot. In 2018, she received ... 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