Route 66's 100th Anniversary: Ranking the Best Road Trip Stretches

As Route 66 approaches its centennial in 2026, a new ranking identifies the most rewarding stretches of the iconic highway, which spans 2,448 miles from Chicago to Santa Monica. The list, published by Quartz, evaluates ten segments based on the survival of the original Route 66 experience, including neon signs, roadside oddities, and pre-interstate diners. Chicago recently moved the official starting point to Navy Pier, with a dedication on March 25, 2026. Seligman, Arizona, is highlighted as the birthplace of the Route 66 revival, thanks to barber Angel Delgadillo, who founded the Historic Route 66 Association of Arizona in 1987. The ranking covers diverse segments: the wild mountain pass between Kingman and Oatman, Arizona; the Mojave Desert crossing to Santa Monica; Oklahoma's 400+ miles of drivable highway; Amarillo's Cadillac Ranch and the Big Texan steak challenge; New Mexico's Tucumcari and the Blue Hole; Springfield, Missouri, where the highway got its number; Kansas's 13.2-mile stretch; and Petrified Forest National Park, which preserves an original alignment. The guide emphasizes that not all stretches are equal, with some retaining original 1926 pavement and others reduced to frontage roads. It serves as both a full itinerary and standalone recommendations for travelers with limited time.