Must stops
Why everyone stops here: The sights that made Route 66 famous

Image: Mateusz Szerszyński
If you’ve ever dreamed about driving the whole Route 66 , or if you ever have, you’ve probably heard about all of these spots. Midpoint Café, Cadillac Ranch, all the way to the Santa Monica Pier… Let’s take a virtual tour from Chicago to Santa Monica, exploring the popular stops along the way!
1
Chicago highlights

Route 66 begins in Chicago, the traditional starting point for east-to-west Route 66 trips; visitors often photograph the "begin" signs and explore nearby city landmarks before hitting the open road.
2
The Gemini Giant

In Wilmington, or the Chain O’ Lakes, you can find another classic. The "Muffler Men" statues, the Gemini Giant towers over a diner and is a favorite selfie station for travelers heading out of Chicago.
3
Pontiac Route 66 Hall of Fame & Murals

In Illinois, Pontiac is a Route 66 museum-and-mural town: murals, classic car collections, and a Route 66 Hall of Fame make it a major cultural stop on the Illinois stretch.
4
Meramec Caverns

Next is Stanton, Missouri: An enormous cave system promoted for decades as a Route 66 attraction; its guided tours and dramatic caverns make it a long-standing draw.
5
Gateway Arch

Of course, there’s the Gateway Arch at St. Louis! The same city provides both the monumental (the Arch) and the kitsch (the famed Ted Drewes custard stands), both popular stops for Route 66 travelers.
6
The Midpoint Café

The official midpoint of Route 66 (halfway between Chicago and Santa Monica) is this Texas diner, "Midpoint," with its famous sign and pies, which are obligatory stops for many road-trippers.
7
Cadillac Ranch

Found in Amarillo, Texas. Ten Cadillacs half-buried nose-first in the dirt, a public, spray-paint-friendly art piece that travelers love to photograph and tag. Interactive, colorful, and instantly iconic.
8
Tucumcari

In New Mexico, you’ll find Tucumcari, famous for neon-lit motels, classic signs, and a lively downtown that celebrates Route 66 nostalgia; photographers and retro lovers linger here for sunsets and signs.
9
10
Albuquerque

A major stopping city with historic Old Town, neon motels, and cultural attractions that pair well with a Route 66 itinerary.
11
Petrified Forest National Park & Painted Desert

Not strictly "roadside kitsch," but these Arizona spots are one of the most spectacular natural detours on Route 66: colorful badlands, fossilized wood, and landscape views tourists remember.
12
Winslow

The Eagles’ song (" Standin’ on the Corner ") turned Winslow’s little corner into a pilgrimage spot; the small park and downtown murals draw fans and photographers.
13
Roy’s Motel & Café

The vast Mojave Desert backdrop , plus the preserved mid-century motel and neon sign, make Amboy, California, one of the most atmospheric stops on the California stretch of Route 66.
14
Santa Monica Pier

Finally, the symbolic end point of Route 66: the famous "End of the Trail" sign and the busy pier make for the classic finish-line photo. It’s touristy, joyful, and unavoidable if you’re completing the westbound route.

























