With summer now officially in full force, I can’t help but fantasize about all the summer road trips I’d like to take. And what evokes the great American road trip more than Route 66? Connecting Chicago to Los Angeles, this 2,400-mile stretch of road has captivated the imagination and incited wanderlust since its completion in 1937.

Although Route 66 was officially decommissioned in 1985, we can still get our kicks and see the vintage vestiges of America’s most famous highway.

6 Must-See Route 66 Attractions

If you’re making the cross-country road trip this year, do it like the old-timers by heading east to west. And, of course, check out these 6 must-see attractions along the way.

1. Grant Park — Chicago, Illinois

Route 66 officially begins right at the entrance of Grant Park. Aside from being the starting point of “The Main Street of America,” Grant Park also hosted the 1893 World’s Fair — where Cracker Jack made its sweet debut and Pabst won its iconic blue ribbon.

What to look for: the “End Historic Route 66” sign.

Where to find it: intersection of Jackson Boulevard and Michigan Avenue, Chicago, Illinois

2. 66 Drive-In — Carthage, Missouri

On such a long journey, you’re going to need some entertainment along the way. Why not stop at one of the few remaining drive-in theaters and catch a flick or 2 (the second movie is free)? A lot has changed since the theater opened in 1949, including the death of the drive-in, but you can watch movies the way road-weary travelers did.

What to look for: the original neon sign, playground, and Art Deco concession stand and ticket booth.

Where to find it: 17231 Old Route 66 Boulevard, Carthage (Brooklyn Heights), Missouri.

3. Milk Bottle Grocery — Oklahoma City, Oklahoma

Route 66 is known for kitsch. And a giant milk bottle crowning a tiny, triangular building spells kitsch like no other. The eponymous grocery store is gone, but in its place is Saigon Baguette. If the sight of all that milk leaves you craving refreshments, stop in for a banh mi (Vietnamese sandwich) and iced coffee.

What to look for: It’s a giant milk bottle. How can you miss it?

Where to find it: 2426 North Classen Boulevard, Oklahoma City, Oklahoma.

4. Cadillac Ranch — Amarillo, Texas

Originally commissioned by Stanley Marsh 3 as an art installation in 1973, Cadillac Ranch is just weird enough to make it one of the most popular tourist attractions along Route 66. After all, where else are you going to find 10 graffitied Cadillacs buried nose-down in the ground?

What to bring: spray paint! Cadillac Ranch is one of the few places where you can release your inner artiste and graffiti to your heart’s content.

Where to find it: along I-40 (old Route 66), just outside Amarillo.

5. Wigwam Village Motel #6 — Holbrook, Arizona

Teepees made of concrete and steel … that you can sleep in! Sure, you could find bigger hotels, but you can’t beat the vintage vibe and the bragging rights. I mean, “have you slept in a wigwam lately?”

What to look for: original handmade hickory furniture, classic cars, and Route 66 memorabilia.

Where to find it: 811 West Hopi Drive, Holbrook, Arizona.

6. Santa Monica Pier — Santa Monica, California

Where Route 66 ends is continually debated. For some, it’s at the intersection of Olympic Boulevard and Lincoln Boulevard. For others, it’s at Santa Monica Boulevard and Ocean Avenue. Regardless of who’s right, Santa Monica Pier has been the de facto end of Route 66. In 2009, it became the official one.

And why not? Where else can you go after you reach land’s end?

What to look for: the historic carousel and hippodrome, Ferris wheel, street performers, and of course, the “end of the trail” sign.

Where to find it: 200 Santa Monica Pier, Santa Monica, California.

Discover more highway history

If you ever wondered about how highways got started anyway, here’s an overview on “the greatest public works project in history.” Plus, the hotly debated history of seat belts.

Travel hacks | Destinations | Getting there


about Anne

If variety is the spice of a copywriter’s life, then Anne’s career at Esurance was akin to sassafras. From 2010 to 2014, she added a touch of zest to topics ranging from cleaning with baking soda to becoming a first-time homeowner.