Route 66 Bucket List Experiences

Last updated on April 21st, 2024 at 09:30 pm

Route 66 runs nearly 2,500 miles across eight states in the United States of America. At every turn of this iconic journey you’ll find a treasure trove of vintage motels glowing neon signs, over-the-top roadside attractions, stunning natural wonders, local restaurants with classic menus, and more. While driving Route 66 is a bucket list experience in itself, the entire journey is filled with Route 66 bucket list experiences and amazing things to do along the way.

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 in search of a better life.

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.

Ready to get inspired? 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

Drive the Entire Length of Route 66

Route 66 Bucket List Experiences - Drive the Entire Length of Route 66

There is no right or wrong way to drive Route 66. You can drive it in stretches doing a section at a time, go state-by-state, or even just get a sampling by visiting some popular attractions on a vacation. 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 by driving straight from Chicago to California without making any stops. At minimum a full Route 66 road trip should take two weeks, but another week or two (or three or four…) will allow you to really get the full experience of The Mother Road.

Drive-Thru Route 66 Sign in Kingman, Arizona Route 66 Roadside Attraction

Watch a Movie at a Route 66 Drive-In Theatre

Route 66 Bucket List Experiences - 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. If you’re looking for a unique activity to add to your road trip itinerary, and Route 66 bucket list, plan to see a drive-in move on your journey! Pull in, grab bucket of popcorn and an extra large Dr Pepper, and enjoy a movie break from the comfort of your car.

Drive-In Movie Theaters on Route 66

Spend the Night in a Classic Motel

Route 66 Bucket List Experiences - Spend the Night in a Classic Motel

Yes, you can stay at a chain hotel on Route 66. There are plenty to choose from! 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 decades or that have been more recently renovated and reopened. Even if you have Hilton points to spare or want an indoor pool and on-site gym along the way, be sure to make room in your itinerary to spend at least a couple nights ditching the chains in favor of sleeping by the soft glow of an iconic neon sign. Check out our list of all the best historic Route 66 hotels and motels worth staying at!

Elvis Suite and Pink Cadillac Bed at Best Western Route 66 Rail Haven Motel in Springfield, Missouri Route 66 Motel

See Iconic Route 66 Roadside Attractions

Route 66 Bucket List Experiences - 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. And you should definitely pull over to take a closer look! There are countless roadside attractions on Route 66, here are just some of the best.

Best Route 66 Roadside Attractions

Blue Whale of Catoosa in Catoosa, Oklahoma Route 66 Roadside Attraction

Learn About Route 66 History at the Museums

Route 66 Bucket List Experiences - Learn About Route 66 History at the Museums

Every state on the Mother Road has its own Route 66 museum that celebrates its history and teaches visitors a thing or two inside. 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.

National Route 66 Museum in Elk City, Oklahoma

Eat at a Famous Restaurant

Route 66 Bucket List Experiences - Eat at a Famous Restaurant

Whether you’re craving a green chile cheeseburger, a chicken fried steak, enchiladas, or a pile of pancakes with a side of eggs and bacon, a big road trip calls for a big meal. There are many places to eat on Route 66: 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.

Cozy Dog Drive In in Springfield, Illinois Route 66 Restaurant

Visit a Vintage Service Station

Route 66 Bucket List Experiences - Take Your Photo with a Route 66 Shield

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 the fuel hasn’t been pumping for years. The vintage service stations on Route 66 keep the spirt of what it was like to drive Route 66 at the start alive. Some of these vintage gas stations have been renovated and others lay in various states of disrepair. But they all showcase different decades of architecture styles and antique fuel pumps they show a very aesthetics far different than what you see today.

Take Your Photo with a Route 66 Shield

Route 66 Bucket List Experiences - Take Your Photo with a Route 66 Shield

The Route 66 shield logos that dot the path from Chicago to California remind you that you’re driving the correct path. Sure, it’s just a traditional road sign, but this iconic symbol 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, and End Points

Route 66 Bucket List Experiences - 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 (and about a mile before!). It’s a rite of passage to stop at them all! Learn more about where Route 66 starts and ends.

Elvis pie at Route 66 Midpoint Cafe in Adrian, Texas - Route 66 restaurant in Texas

See a Route 66 Muffler Man

Route 66 Bucket List Experiences - 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. Muffler Men are popular Route 66 roadside attractions, so popular that you can find both original and brand new fiberglass giants in many places across the main street of America.

NAU Skydome Lumberjack Muffler Man in Flagstaff, Arizona Route 66 Roadside Attraction

Buy a Route 66 Souvenir

Route 66 Bucket List Experiences - Buy a Route 66 Souvenir

Mugs, magnets, t-shirts, keychains, postcards, bumper stickers, shot glasses, pins. There are a lot of options when it comes to choosing the perfect 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 - 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.

Meramec Caverns in Sullivan, Missouri

Stop at a National Park

Route 66 Bucket List Experiences - Stop at a National Park

There are many state parks, national monuments, memorials, and 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, it is close enough that many travelers make the detour or take a train for a day trip from Williams.

If you love the outdoors, want to explore the country’s natural beauty, or just want an excuse to stretch your legs, a stop at a national park is a must for your Route 66 bucket list.

Find a Route 66 Mural

Route 66 Bucket List Experiences - Find a Route 66 Mural

Murals are becoming a 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! Pull over to take fun photos in front of them.

Find the Stops and People That Inspired the Movie Cars

Route 66 Bucket List Experiences - 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, Hackberry General Store, and Seligman, Arizona are all represented in the movie. Plan your road trip to check out all the Cars locations on Route 66.

Cars on the Route in Galena, Kansas Route 66 Roadside Attraction

Bask in the Glow of a Neon Sign

Route 66 Bucket List Experiences - 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 across Route 66. Businesses old and new embrace the neon with bright, colorful signs that light up their businesses at night. Leave your motel room after dark to bask in their glow!

Drive on an Original Stretch of Route 66 Road

Route 66 Bucket List Experiences - 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 long 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 Mother Road.

Download this List of Route 66 Bucket List Experiences

Route 66 Bucket List Experiences Free Printable Download

Download this free printable Route 66 bucket list PDF! Print it out and check off your bucket-list worthy experiences as you go. How many will you finish on your way from Chicago to Los Angeles?

Plan Your Route 66 Road Trip

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Last modified: April 21, 2024
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