Route 66 has officially turned 100—and America’s most mythologized stretch of asphalt is glowing a little bit brighter in 2026. Extending nearly 2,500 miles across eight states, from Chicago to Santa Monica, the Mother Road has long been more than a mere road trip route. Instead, it’s a living postcard of neon motel signs, dusty diners, desert horizons, and a special essence of Americana, ever-suspended in technicolor. While the road is no longer considered an “official” US highway, it’s the iconic stops—the hotels, motels, and roadside inns—along the way that honor its legacy and kitschy ol’ soul.
From glowing midcentury motor lodges to quirky roadside stays, Route 66’s timeless properties are just as essential to the journey as Amarillo’s Cadillac Ranch or the Santa Monica Pier. Some remain wonderfully frozen in time, while others are thoughtfully restored with a more tasteful, design-forward edge. All of these sites, though, are magnetic—pulling you off the road and into an era, or a story, entirely of their own.
This year, the nation’s most beloved highway will be in full-blown celebration mode with loads of parades, vintage car rallies, art shows, and festivals to celebrate its 100th birthday. Whether you are already planning to hit the road or looking for a reason to get in gear, consider this your big neon sign to check into the historic hideaways and classic roadside icons that define Route 66’s timeless, somehow forever-nostalgic soul.
Read on for the best hotels and inns to book along Route 66, starting with properties in Chicago, the unofficial starting point, and ending with accommodations in Santa Monica, the end of the trail. These gems serve as living time capsules for the joint celebration happening this year: Route 66’s centennial and America’s 250th birthday.
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Top picks:
- For a stellar launching pad: Palmer House in Chicago, Illinois
- For neon-lit nostalgia: Blue Swallow Motel in Tucumari, New Mexico
- For a spot that’s worth the short detour: El Rey Court in Santa Fe, New Mexico
- For a glamorous final scene: The Georgian in Santa Monica, California