La Posada is more than a place to sleep, it’s a living piece of Route 66 history. Opened in 1930 to welcome Santa Fe Railway passengers to Winslow, Mary Colter designed the hotel as a Spanish hacienda, hosting icons like John Wayne, Albert Einstein and Amelia Earhart. After narrowly escaping demolition, it has been beautifully restored. Today, dig into crispy pork carnitas at the Turquoise Room, wander the restored Sunken Garden, and explore galleries showcasing Navajo weaving and regional art.

Follow the rabbit billboard trail to Joseph City’s Jack Rabbit Trading Post, a Route 66 classic built on brilliant marketing. A series of spaced out signs once teased motorists with “HERE IT IS,” turning anticipation into arrival. Today the trading post still welcomes travelers, complete with a giant fiberglass jackrabbit you can ride. Inside, Route 66 souvenirs keep the legend alive at one of the Mother Road’s most iconic stops.

In Flagstaff, history lives both on the roadside and beneath it. The Flagstaff Underground Tour leads visitors below downtown streets into hidden basements and steam tunnels tied to Route 66-era buildings. Built in part during the 1920s to heat the business district, the corridors connect former saloons and even an underground bowling alley. Along the way, guides share tales of bootlegging, gambling raids and frontier rivalries that shaped the city’s Wild West past.

The silhouette says it all. In Holbrook, 15 concrete teepees rise from the desert at the Wigwam Motel, transforming a simple overnight stay into a Route 66 rite of passage. Built for the automobile age, each freestanding 32 foot “wigwam” houses a single room, blending vintage charm with modern comforts like air conditioning. Family operated since 1938, this National Register landmark keeps roadside nostalgia alive near Petrified Forest National Park.

At Antares Point in northwestern Arizona, Giganticus Headicus rises 14 feet above Route 66, a bright green tiki style guardian of the highway. Created in 2004 by artist Gregg Arnold, the cement sculpture nods to the Mother Road’s tradition of bold, offbeat roadside attractions. Echoing the monumental figures of Easter Island, it transforms pure spectacle into an open invitation to pull over, snap a photo and celebrate the playful spirit of America’s most storied highway.

On a quiet stretch of Route 66 between Seligman and Kingman, the Hackberry General Store delivers wall to wall nostalgia. Opened in the early 1930s as a grocery and gas stop, it evolved from ranch supply outpost to full blown Mother Road landmark. Vintage pumps, weathered signs and classic cars crowd the exterior, while inside Route 66 memorabilia turns the space into part museum, part time capsule of American road travel.

Come for the dome, stay for the dinosaurs. Meteor City began in 1938 as a Texaco gas station serving travelers bound for nearby Meteor Crater. Over time it evolved into a full-fledged roadside attraction, crowned by a mohawk-topped geodesic dome added in 1979. Restored and reopened in 2025 as the Dino Drive-Thru, the site now pairs Route 66 memorabilia and murals with a drive-through of life-sized animatronic dinosaurs.

Tickled Pink Flamingos swaps neon glow for wide open night skies along Route 66 near Holbrook. This off grid campground and retreat center blends travel with creativity, hosting workshops, author talks and storytelling programs rooted in personal narrative and nature. Just a short drive from Petrified Forest National Park, it reflects a new chapter of the Mother Road, inviting travelers to slow down, stay awhile and gather in community.