Route 66 Bucket List Experiences: Things to Do on Route 66

Route 66 runs nearly 2,500 miles across cover across eight states. At every turn you’ll find a treasure trove of vintage motels, roadside attractions, natural wonders, iconic restaurants, and more. While driving Route 66 is a bucket list experience in itself, the journey is filled with Route 66 bucket list experiences and amazing things to do.

Historic U.S. Route 66 (AKA US 66, the Will Rogers Highway, Main Street of America, and the Mother Road) was established on November 11, 1926. It was the primary road that travelers took while moving west during the dust bowl. Covering around 2,448 miles from Chicago, Illinois to Santa Monica, California, Route 66 took travelers through Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California.

Although Route 66 was removed from the United States Highway System in 1985, it is still a popular bucket-list worthy road trip route for travelers looking for a sense of vintage nostalgia.

If you’re planning a Route 66 road trip, be sure to add this list of things to do on Route 66 to your travel itinerary and Route 66 bucket list.

Route 66 Bucket List Experiences: Things to Do on Route 66

Drive the Entire Length of Route 66

Route 66 Bucket List Experiences and Things to Do on Route 66: Drive the Entire Length of Route 66

There’s no right or wrong way to drive Route 66. You can drive it in stretches doing a section at a time or go state-by-state. But to truly get the full experience of the Mother Road, plan to drive the entire 2,400 miles from Chicago to Santa Monica in one go. It’s truly a bucket list worthy road trip. Just don’t rush it: there are plenty of things to do on Route 66 and you don’t want to miss a thing bu driving without stops. At minimum a full Route 66 road trip should take two weeks, but four weeks will allow you to really get the full experience.

Watch a Movie at a Route 66 Drive-In Theatre

Route 66 Bucket List Experiences and Things to Do on Route 66: Watch a Movie at a Route 66 Drive-In Theatre

Drive-in movie theaters are alive and well on Route 66. Though there are not quite as many operating as there were in their heyday, several drive-ins are still operating today. So pull up, grab some popcorn, and enjoy a movie break on your road trip.

Route 66 Drive-In Theatres

  • The Litchfield Skyview Drive-In Theater in Litchfield, Illinois
  • Route 66 Drive In Theater in Springfield, Illinois
  • 66 Drive-In Theatre in Carthage, Missouri
  • Admiral Twin Drive-In Theater in Tulsa, Oklahoma
  • Teepee Drive-in Theater in Sapulpa, Oklahoma
  • Azusa Foothill Drive-In in Azusa, California

Spend the Night in a Classic Motel

Route 66 Bucket List Experiences and Things to Do on Route 66: Spend the Night in a Classic Motel

Sure, you can stay at a chain hotel on Route 66. But if you really want an authentic experience, you have to stay at some of the classic motels on Route 66. There are numerous vintage hotels, motels, and motor courts that have been around for years or that have been renovated and reopened. Check out our list of all the historic Route 66 hotels and motels worth staying at!

Elvis Suite at the Best Western Route 66 Rail Haven Motel in Springfield, Missouri

Sleep like a King

Spend the night dreaming in a pink Cadillac bed in the room where Elvis slept. Book a night at the Elvis Suite at the Rail Haven motel in Springfield, Missouri.

See Iconic Route 66 Roadside Attractions

Route 66 Bucket List Experiences and Things to Do on Route 66: See Iconic Route 66 Roadside Attractions

You can barely drive a mile on Route 66 without running into an iconic roadside attraction. Those big, weird things that were made to get you to pull over to take a closer look. Here are just some of the best roadside attractions on Route 66.

Best Route 66 Roadside Attractions

Learn About Route 66 History at the Museums

Route 66 Bucket List Experiences and Things to Do on Route 66: Learn About Route 66 History at the Museums

Every state on the Mother Road has its own Route 66 museum that celebrates its history. There is also a National Route 66 museum in Oklahoma and a wide variety of other museums dedicated to everything from vintage cars to barbed wire to McDonald’s. Be sure to add a few of these museums to your travel itinerary and Route 66 bucket list. Check out a full list of Route 66 Museums to visit.

Eat at a Famous Restaurant

Route 66 Bucket List Experiences and Things to Do on Route 66: Eat at a Famous Restaurant

Whether you’re craving a green chile cheeseburger, a chicken fried steak, or a pile of pancakes, a big road trip calls for a big meal. There are many places to eat on Route 66 to choose from: drive-throughs, diners, cafes, and more. Start your road trip in Chicago at the famous Lou Mitchell’s Restaurant, pull over for ugly crust pie at the Midpoint Cafe in Texas, and don’t skip Delgadillo’s Snow Cap Drive-In in Arizona.

Corn dog and fries at Cozy Dog Drive In in Springfield, Illinois on Route 66

Where the Corn Dog was Born

A juicy hot dog skewered on a stick, coated in a thick corn laden batter, and deep fried to a crunchy golden brown. Get a taste of history at this Route 66 institution: Cozy Dog Drive In in Springfield, Illinois.

Visit a Vintage Service Station

Route 66 Bucket List Experiences and Things to Do on Route 66: Visit a Vintage Service Station

With 2,400 miles to drive, you’re going to need to pull over to fuel up at a lot of gas stations. But you also might pull over at a lot of gas stations where fuel hasn’t been running for years. The vintage service stations on Route 66 keep alive the spirt of what it was like to drive Route 66 at the start. Some have been renovated and other lay in various states of disrepair. They all showcase different decades of architecture style and antique fuel pumps they show a very different aesthetic than what you see today.

Take Your Photo with a Route 66 Shield

Route 66 Bucket List Experiences and Things to Do on Route 66: Take Your Photo with a Route 66 Shield

The shield logo that tells you you’re on the correct path and is an iconic symbol of the iconic road. Sure, it’s just a traditional road sign, but it truly represents the journey. You’ll find the shield on road signs, businesses, souvenirs, and painted across the road. In each state the logo changes to include whichever of the 8 states you’re currently traveling in. Be sure to get your photo with one or all of these iconic markers.

Stop at the Beginning, Middle, End Points

Route 66 Bucket List Experiences and Things to Do on Route 66: Stop at the Beginning, Middle, End Points

Did you really drive all of Route 66 if you didn’t stop at the waypoints along the way? Most famously, there are begin signs in Chicago, a midpoint sign in Texas, and an end sign on the Santa Monica Pier. It’s a rite of passage to stop at them all! Learn more about where Route 66 starts and ends.

See a Route 66 Muffler Man

Route 66 Bucket List Experiences and Things to Do on Route 66: See a Route 66 Muffler Man

Muffler men roadside attractions are fiberglass giants who stand anywhere from 14 to 25 feet tall. Each has a similar design and was built between 1963 and 1972 by International Fiberglass in Venice, California. With signature stances, these big men stood outside of muffler shops and other businesses to call attention from the road. You’ll find many muffler men on Route 66.

Muffler Men on Route 66

Buy a Route 66 Souvenir

Route 66 Bucket List Experiences and Things to Do on Route 66: Buy a Route 66 Souvenir

Mugs, magnets, t-shirts, keychains, postcards, bumper stickers, pins. There are a lot of options when it comes to choosing a Route 66 souvenir. Whatever you collect, definitely plan to pick up a few Route 66 souvenirs to commemorate your epic adventure. Look for specialty souvenir shops on Route 66, like Buck Atom’s Cosmic Curios and the Uranus Fudge Factory and General Store.

Explore a Cavern

Route 66 Bucket List Experiences and Things to Do on Route 66: Explore a Cavern

There are several caverns on Route 66. You can take a short detour to explore the Grand Canyon Caverns or stop at Fantastic Caverns. But none is so talked about than Meramec Caverns. You’ll see billboards for the attraction for miles upon miles and even might see a famous painted barn a state or so away. Whichever you choose, caverns give you a breathtaking look underground.

Stop at a National Park

Route 66 Bucket List Experiences and Things to Do on Route 66: Stop at a National Park

There are many state parks, national monuments, memorials, forests along the path of Route 66. The two biggest national parks on Route 66 are the Petrified Forest National Park and Grand Canyon National Park in Arizona. While the Grand Canyon isn’t technically located on Route 66, t is close enough that many travelers make the detour or take a train for a day trip from Williams.

Find a Route 66 Mural

Route 66 Bucket List Experiences and Things to Do on Route 66: Find a Route 66 Mural

Murals are becoming more and more popular way to build a monument to Route 66 and pay homage to the past. You can find plenty of Route 66 murals along the Mother Road. Look for them in the small towns and big cities along the way!

Find the Stops and People That Inspired the Movie Cars

Route 66 Bucket List Experiences and Things to Do on Route 66: Find the Stops and People That Inspired the Movie Cars

The popular Pixar movie Cars and its fictional setting of Radiator Springs took much inspiration from Route 66. Places like Cars on the Route, the U-Drop Inn, Wigwam Motel, and Hackberry General store are all represented in the movie. Plan your road trip to check out all the Cars locations on Route 66.

Bask in the Glow of a Neon Sign

Route 66 Bucket List Experiences and Things to Do on Route 66: Bask in the Glow of a Neon Sign

You might not even need to sun to light your way down Route 66. The glow of neon signs illuminates the Mother Road. Neon signs can be found at motels, restaurants, tourist attractions, gift shops, and more. There’s even a new neon park in Tulsa!

Drive on an Original Stretch of Route 66 Road

Route 66 Bucket List Experiences and Things to Do on Route 66: Drive on an Original Stretch of Route 66 Road

Route 66 was decommissioned in 1985. While most of route was replaced with the modern highway system, you can still drive a large chunk of the actual way. Still, most of those roads have been paved over. There are still some stretches throughout the journey that still boast the original road. Make it a part of your bucket list journey on Route 66 to drive on some of the original road.

Pin this list of Route 66 Bucket List Experiences and Things to Do on Route 66

Route 66 runs nearly 2,500 miles across cover across eight states. At every turn you'll find a treasure trove of vintage motels, roadside attractions, natural wonders, iconic restaurants, and more. While driving Route 66 is a bucket list experience in itself, the journey is filled with Route 66 bucket list experiences and amazing things to do. If you're planning a Route 66 road trip, be sure to add this list of things to do on Route 66 to your travel itinerary and Route 66 bucket list. #Route66
Route 66 runs nearly 2,500 miles across cover across eight states. At every turn you'll find a treasure trove of vintage motels, roadside attractions, natural wonders, iconic restaurants, and more. While driving Route 66 is a bucket list experience in itself, the journey is filled with Route 66 bucket list experiences and amazing things to do. If you're planning a Route 66 road trip, be sure to add this list of things to do on Route 66 to your travel itinerary and Route 66 bucket list. #Route66

VALerie BROMANN

Founder & Head Road Tripper

Val is the founder and head road tripper at Silly America. Having grown up near Berwyn's famed car kabob, The Spindle, and a restaurant with a cow on its roof, her fascination with roadside attractions started early. Today, Val has visited hundreds roadside attractions across the United States and is constantly on the lookout for the next BIG thing!