Historic Route 66, Flagstaff to Winslow

Route 66 was commissioned in 1926 as one of the first federal highways, linking Chicago to Los Angeles, and it quickly became the road of American migration and imagination. In the 1930s it carried families fleeing the Dust Bowl toward California, a journey the writer John Steinbeck immortalized when he called it the Mother Road. Later it became the route of the postwar vacation, lined with motor courts, trading posts, and roadside attractions.

This part of the highway crosses land long home to Native peoples, including the Hopi and Navajo (Diné), whose lands lie to the north and east, and the railroad towns along the route grew up as service stops on the Santa Fe line. When Interstate 40 bypassed the old road town by town in the later twentieth century, many of those communities struggled, and the movement to remember and preserve Route 66 grew out of that loss, keeping the neon lit and the stories alive.

Flagstaff anchors the western end of this drive, a mountain town at about 7,000 feet beneath the San Francisco Peaks, the highest mountains in Arizona. Route 66 runs right through its walkable historic downtown, where the railroad still rumbles past old brick buildings, red-brick hotels, and vintage signs, and the pine forest presses close on every side.

The town is a world apart from the desert to the east, cool and green, with dark night skies that made it home to Lowell Observatory, where Pluto was discovered. For travelers on 66 it has long been a natural resting point, a place to overnight in the pines before dropping down toward the open country beyond, and its blend of college town, railroad town, and mountain town gives it a lively character all its own.

As the road runs east from Flagstaff, the pines thin and fall away and the land opens into high desert, wide and dry, with the horizon stretching toward the Painted Desert and the mesas of the Navajo and Hopi country. The air warms, the sky grows huge, and the drive takes on the lonesome, wide-open feeling that Route 66 is famous for.

Winslow waits at the eastern end, a railroad town that fell quiet after the interstate bypassed it and then found new life in an unexpected way. A single line in the Eagles' song Take It Easy, about standing on a corner in Winslow, Arizona, put it back on the map, and the town built a park around the lyric that draws travelers to this day. Winslow is also home to La Posada, a beautifully restored railroad hotel and one of the finest surviving works of the architect Mary Colter, a fitting reward at the end of the drive.

Spring and fall are ideal for this drive, with mild weather at both ends and comfortable temperatures for wandering the small towns and stopping at the roadside sights. Summer is warm and lively, especially in the desert stretch, though Flagstaff's high elevation keeps its end pleasantly cool even in July.

Winter transforms the western end, when snow settles over Flagstaff and the pines while the desert around Winslow stays milder, so the drive can carry you from a snowy mountain town to open, sunlit high desert in a single afternoon. That contrast is part of what makes this a rewarding stretch of the Mother Road in any season.

The closest Boutel™ stays, so you can turn this stop into an overnight. Each is an independently owned, editorially selected place to stay.